9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester |
 |
| Name | 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester | ||
| Synonyms | |||
| Name in Chemical Abstracts | 2-Furannonanoic acid, tetrahydro-5-oxo-, methyl ester | ||
| CAS No | 22623-86-5 | ||
| Molecular formula | C14H24O4 | ||
| Molecular mass | 256.35 | ||
| SMILES code | O=C1OC(CC1)CCCCCCCCC(=O)OC | ||
| 1H-NMR: 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester | |||
| 500 MHz, CDCl3 | |||
| delta [ppm] | mult. | atoms | assignment |
| 1.24-1.45 | m | 10 H | 4-H, 5-H, 6-H, 7-H, 8-H |
| 1.57 | m | 2 H | 3-H |
| 1.70 | m | 1 H | 9-H |
| 1.82 | m | 1 H | 9-H |
| 2.27 | t | 2 H | 2-H |
| 2.30 | m | 2 H | 3-H (ring) |
| 2.50 | m | 2 H | 4-H (ring) |
| 3.67 | s | 3 H | O-CH3 |
| 4.48 | m | 1 H | 2-H (ring) |
13C NMR
| 13C-NMR: 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester | |||
| 125.7 MHz, CDCl3 | |||
| delta [ppm] | assignment | ||
| 24.9 | C3 | ||
| 25.2 | C9 | ||
| 28.0-29.2 | C4, C5, C6, C7, C8, C3 (ring) | ||
| 34.0 | C2 | ||
| 35.5 | C4 (ring) | ||
| 51.4 | O-CH3 | ||
| 81.0 | C2 (ring) | ||
| 174.2 | C1 (O-C(=O)-) | ||
| 177.2 | C5 (O-C(=O)-, ring) | ||
| 76.5-77.5 | CDCl3 | ||
IR |
| IR: 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester | |||
| [Film, T%, cm-1] | |||
| [cm-1] | assignment | ||
| 2931, 2856 | aliph. C-H valence | ||
| 1776 | C=O valence, lactone | ||
| 1737 | C=O valence, ester | ||
| Cu |
     |
Synthesis of 9-(5-oxotetrahydrofuran-2-yl)nonanoic acid methyl ester |
| Reaction type: | addition to alkenes, radical reaction, ring closure reaction |
| Substance classes: | alkene, halogencarboxylic acid ester, lactone |
| Techniques: | working with cover gas, stirring with magnetic stir bar, heating under reflux, evaporating with rotary evaporator, filtering, recrystallizing, heating with oil bath |
| Degree of difficulty: | Easy |
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE
Join me on twitter
Join me on google plus 
Googleplus
Googleplus
amcrasto@gmail.com
Operating scheme
Instructionshttp://www.oc-praktikum.de/nop/en/instructions/pdf/4005_en.pdf
Instruction (batch scale 100 mmol)
Equipment 250 mL two-neck flask, protective gas supply, reflux condenser, heatable magnetic stirrer, magnetic stir bar, rotary evaporator, Buechner funnel, suction flask, desiccator, oil bath Substances undecenoic acid methyl ester (bp 248 °C) 19.8 g (22.3 mL, 100 mmol) iodoacetic acid ethyl ester (bp 73-74 °C/ 21 hPa) 27.8 g (15.4 mL, 130 mmol) copper powder (finely powdered, >230 mesh ASTM) 30.5 g (480 mmol) tert-butyl methyl ether (bp 55 °C) 130 mL petroleum ether (bp 60-80 °C) 300 mL Reaction In a 250 mL two-neck flask with magnetic stir bar and a reflux condenser connected with a protective gas piping 19.8 g (22.3 mL, 100 mmol) undecenoic acid methyl ester and 27.8 g (15.4 mL, 130 mmol) iodoacetic acid ethyl ester are mixed with 30.5 g (480 mmol) copper powder under a protective gas atmosphere. Afterwards the reaction mixture is stirred at 130 °C oil bath temperature under protective gas for 4 hours. (Reaction monitoring see Analytics.)
Work up The reaction mixture is cooled down to room temperature, 30 mL tert-butyl methyl ether are added, the mixture is stirred for 5 minutes and filtered off. The copper powder on the filter is washed four times with 25 mL tert-butyl methyl ether each. Filtrates and wash solutions are combined, the solvent is evaporated at the rotary evaporator. A yellow oil remains as crude product. Crude yield: 25.4 g.
The crude product is dissolved in 300 mL petroleum ether under reflux. The solution is allowed to cool down to room temperature, then it is stored in the refrigerator over night for complete crystallization. The crystalline product is sucked off over a Buechner funnel and dried in the vacuum desiccator. The mother liquor is stored again in the refrigerator for a check of complete crystallization. Yield: 19.5 g (76.1 mmol, 76%); white solid, mp 34 °C Comments In order to achieve a quantitative reaction within 4 hours, a fivefold excess of copper is used.
Waste management Recycling The copper powder can be used three times.
Waste disposal Waste Disposal evaporated tert-butyl methyl ether (might contain iodoethane) organic solvents, containing halogen mother liquor from recrystallization organic solvents, containing halogen copper powder solid waste, free from mercury, containing heavy metals
Time 6-7 hours
Break After heating and before recrystallizing
Degree of difficulty Easy
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE
Join me on twitter
Join me on google plus Googleplus
Googleplus
amcrasto@gmail.com
Analytics Reaction monitoring with TLC Sample preparation: Using a Pasteur pipette, two drops of the reaction mixture are taken and diluted with 0.5 mL diethyl ether. TLC-conditions: adsorbant: TLC-aluminium foil (silica gel 60) eluent: petroleum ether (60/80) : acetic acid ethyl ester = 7 : 3 visualisation: The TLC-aluminium foil is dipped in 2 N H2SO4 and then dried with a hot air dryer. Reaction monitoring with GC Sample preparation: Using a Pasteur pipette, one drop of the reaction mixture is taken and diluted with 10 mL dichloromethane. From this solution, 0.2 µL are injected. 10 mg from the solid product are dissolved in 10 mL dichloromethane. From this solution, 0.2 µL are injected. GC-conditions: column: DB-1, 28 m, internal diameter 0.32 mm, film 0.25 µm inlet: on-column-injection carrier gas: hydrogen (40 cm/s) oven: 90 °C (5 min), 10 °C/min to 240 °C (40 min) detector: FID, 270 °C Percent concentration was calculated from peak areas.
Chromatogram |
| GC: crude product | |
| column | DB-1, L=28 m, d=0.32 mm, film=0.25 µm |
| inlet | on column injection, 0.2 µL |
| carrier gas | H2, 40 cm/s |
| oven | 90°C (5 min), 10°C/min –> 240°C (40 min) |
| detector | FID, 270°C |
| integration | percent concentration calculated from relative peak area |
| GC: pure product | |
| column | DB-1, L=28 m, d=0.32 mm, film=0.25 µm |
| inlet | on column injection, 0.2 µL |
| carrier gas | H2, 40 cm/s |
| oven | 90°C (5 min), 10°C/min –> 240°C (40 min) |
| detector | FID, 270°C |
| integration | percent concentration calculated from relative peak area |
Substances required |
| Batch scale: | 0.01 mol | 0.1 mol | 10-Undecenoic acid methyl ester |
| Educts | Amount | Risk | Safety | ||||||
|---|---|---|---|---|---|---|---|---|---|
| 10-Undecenoic acid methyl ester | 19.8 g | H- EUH- | P- | ||||||
| Iodoacetic acid ethyl ester |
|
27.8 g | H300 H314 EUH- | P264 P280 P305 + 351 + 338 P310 | |||||
| Reagents | Amount | Risk | Safety | ||||||
| Copper powder |
|
30.5 g | H400 EUH- | P273 | |||||
| Solvents | Amount | Risk | Safety | ||||||
| tert-Butyl methyl ether |
|
130 mL | H225 H315 | P210 | |||||
| Petroleum ether (60-80) |
|
300 mL | H225 H304 H315 H336 H411 EUH- | P210 P261 P273 P301 + 310 P331 | |||||
| Others | Amount | Risk | Safety | ||||||
| Sulfuric acid 2N |
|
H314 H290 EUH- | P280 P301 + 330 + 331 P305 + 351 + 338 P309 + 310 | ||||||
| Solvents for analysis | Amount | Risk | Safety | ||||||
| Petroleum ether (60-80) |
|
H225 H304 H315 H336 H411 EUH- | P210 P261 P273 P301 + 310 P331 | ||||||
| Acetic acid ethyl ester |
|
H225 H319 H336 EUH066 | P210 P261 P305 + 351 + 338 | ||||||
| Dichloromethane |
|
H351 H315 H319 H335 H336 H373 | P261 P281 P305 + 351 + 338 |
Substances produced |
| Batch scale: | 0.01 mol | 0.1 mol | 10-Undecenoic acid methyl ester |
| Products | Amount | Risk | Safety | |
|---|---|---|---|---|
| 9-(5-Oxotetrahydrofuran-2-yl)nonanoic acid methyl ester |
Equipment |
| Batch scale: | 0.01 mol | 0.1 mol | 10-Undecenoic acid methyl ester |
 |
two-necked flask 250 mL |  |
protective gas piping | |
 |
reflux condenser |  |
heatable magnetic stirrer with magnetic stir bar | |
 |
rotary evaporator |  |
suction filter | |
 |
suction flask |  |
exsiccator with drying agent | |
 |
oil bath |
Simple evaluation indices |
| Batch scale: | 0.01 mol | 0.1 mol | 10-Undecenoic acid methyl ester |
| Atom economy | 53.9 | % | |
| Yield | 76 | % | |
| Target product mass | 19.5 | g | |
| Sum of input masses | 370 | g | |
| Mass efficiency | 53 | mg/g | |
| Mass index | 19 | g input / g product | |
| E factor | 18 | g waste / g product |
Share this:
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE
Join me on twitter
Join me on google plus Googleplus
Googleplus
amcrasto@gmail.com
EAST TIMOR
Nicolau Lobato Airport (DIL), Dili, Timor-Leste
DILI
BORDER WITH INDONESIA
Political division of Timor
- TimorIsland in Indonesia
- Timor is an island at the southern end of Maritime Southeast Asia, north of the Timor Sea. The island is divided between the sovereign states of East Timor, on the eastern part, and Indonesia, on the western part.Wikipedia
My Top Restaurants in Dili – Timor Leste (East Timor)
Dili
is a small and humble town with a few restaurants here and there. For
those of you that are accustomed to high luxury 5 star courses, you will
be hard pressed to be in Dili and enjoy its cuisine. However, if you
are adventurous and especially can appreciate the small things in life,
you will be very pleased with what Dili has to offer. The below list
are the top places I stumbled across my travels there.
German style Winerschnitzel at “One more Bar”.
1) One More Bar restaurant is located at the famous Avenida dos Dereitos Humanos. (Tel: 723-5593) and opens 7 days a week. This is an Australian bar catering mostly to UN expats living in Dili. Its second story bar gives you a beautiful look towards the ocean with wondrous Timor-Leste sunsets. However, don’t be fooled as this is not your romantic venue. This fun-loving joint maintains action packed nights with live music every Friday and an All Sports Live theme. Its grub is mostly Western ranging at the $10-$15 US dollar price range. During my visit in Dili, I enjoyed the day’s special German styled Winerschnitzel with handmade mashed potatoes and fresh veggies. I should have left the gravy on the side. It hit the spot completely along with long tall beer. My bill was about $12 US dollars. Highly recommend the bar’s Egg Benedict priced at $7.50 US dollars for your next morning meal.
Entrance to “Little Pattaya” restaurant.
2) Little Pattaya is Thai-Lebanese restaurant located at right before the “White Sand” Beach on its coastal roads. The owners are a married couple, one is Lebanese, the other one is Thai and they split their restaurant’s menu between Thai dishes and Lebanese dishes. This place has great atmosphere and its sitting arrangements right at the beach can melt the toughest heart. It overlooks the majestic mountains of Timor-Leste with the famous Jesus statue looking over your shoulder. A decent Thai meal will cost roughly $5-$7 US dollars per plate. I tried the Chicken in Cashew Nuts ($5 US) with a nice Lychee Fruit Shake ($3 US). I followed the evening with several Bintang beers ($5 US) enjoying the ocean right in front of me. The restaurants grilled fish (priced at its catch size) is high on my list on things to do next. I have a passion for Thai food and having this restaurant in Dili is a life saver! Note: “Farang” dishes also available.
Little Pattaya restaurant in Dili has tables on the beach.
3) Kebab Club restaurant is located at the Rua Belarmino Lobo (Tel: +670-7297-121) close to the beach. If you are not looking closely it is very easy to miss. Try arriving at about 5pm when the grilled kebabs begin cooking. The meals have an authentic feel and its bread making is divine and special. Fresh baked breads on Tuesdays and Saturdays. I keep coming back for the Baklava! Some items can get pricey. Look at spending anywhere from $3 – $20 US dollars.
The Kebab Club restaurant in Dili.
4) Discovery Inn – DIYA Restaurant is located at Avenida Presidente Nicolau Lobato (Tel: +670-331-1111). This is the best and closes to luxury dining that you can get in Dili. It’s elegant and tropical feel entrance to Diya is quiet and welcoming. The restaurant is quite beautiful inside and the staff is neatly dressed and ready to assist. All speak English and make recommendations. I loved the meatballs, steaks, and pasta dishes. My heart remained at Diya for their home-made Molten Lava Chocolate Cake. It was heavenly! Now, don’t be surprised that you can walk out of this humble, luxury restaurant with a price tag of about $25-$30 US dollars per person for a dinner experience. If you find yourself in Dili with your special other on an anniversary, birthday, or just a nice romantic evening, this is the place to be.
Caz Bar restaurant in Dili.
5) Caz Bar restaurant is located at the heart of “White Beach” (Tel: +670-723-3961) past the Hera turn. During an early hike to the Statue of Jesus, I left this beautiful monument hungry and ready for some relaxing time. I walked a good 20 min. to finally reach the Caz Bar. My attention was captured by the number of foreigners sitting at this serene white beach enjoying the morning day – reading books, swimming, or simply just talking. Most of the expats make this a weekly weekend event. I took a table under a tree and ordered my breakfast. Delicious French styled Crepe with Nutella ($2.50 US) – yes Nutella in Dili, some cold Soda water, and a cup of coffee. I’ll be back next Saturday morning.
Caz Bar restaurant in Dili – foreigner beloved place.
6) Ocean Viewrestaurant is located at Bebonuk (Tel: +670-723-6041) on the Northern end of Dili. Are you in the mood for hardy Seafood? This is your place. The restaurant sports an awesome deck overlooking the ocean and bringing its seafood delights right to your table. I devoured the day’s special grilled Lobster ($20 US), fried Calamari for starters, and boiled Chinese dumplings. Yes, I know the dumplings were an odd combination but a delicious one! A Tiger Beer complimented the dinner and left me satisfied with this search. Thai food is also available!
Ocean view restaurant – seafood paradise.
So, that is my list of my top restaurants in Dili. I know I have left several others and welcome your input. My last comment is for those that need their fast food fix.
Eastern burger fast food restaurant in Dili.
7) Eastern Burgerfast food restaurant is located at the Avenida Presidente Nicolau Lobato just walking distance from the Discovery Inn and the famous ANZ Bank. The Eastern Burger caters to the town’s teenagers and young families on the weekend. This piece of American fast food inspired dishes carries a Beef Burger Combo to include drink and fries ($3.50 US), Egg Burger ($2 US), Hot Dog ($2.50 US) along with Asian styled fast food like Dumpling Noodle soup ($4.50 US) and Curry Chicken Rice Set ($5 US). Other oddities include Peanut Butter and Milk Set ($1 US) and even stranger is the French toast with cheese AND Peanut Butter ($3 US). The Eastern Burger restaurant packs a crowd. The food is fresh and served with a warm smile.
Eastern burger restaurant is visited by local kids and young families.
8) After your Eastern Burger bonanza, cross the street and find Dili’s ice cream shop –Que Bom.
Que Bom ice cream shop in Dili.
It’s only our first evening in Dili
German style Winerschnitzel at “One more Bar”.
1) One More Bar restaurant is located at the famous Avenida dos Dereitos Humanos. (Tel: 723-5593) and opens 7 days a week. This is an Australian bar catering mostly to UN expats living in Dili. Its second story bar gives you a beautiful look towards the ocean with wondrous Timor-Leste sunsets. However, don’t be fooled as this is not your romantic venue. This fun-loving joint maintains action packed nights with live music every Friday and an All Sports Live theme. Its grub is mostly Western ranging at the $10-$15 US dollar price range. During my visit in Dili, I enjoyed the day’s special German styled Winerschnitzel with handmade mashed potatoes and fresh veggies. I should have left the gravy on the side. It hit the spot completely along with long tall beer. My bill was about $12 US dollars. Highly recommend the bar’s Egg Benedict priced at $7.50 US dollars for your next morning meal.
Entrance to “Little Pattaya” restaurant.
2) Little Pattaya is Thai-Lebanese restaurant located at right before the “White Sand” Beach on its coastal roads. The owners are a married couple, one is Lebanese, the other one is Thai and they split their restaurant’s menu between Thai dishes and Lebanese dishes. This place has great atmosphere and its sitting arrangements right at the beach can melt the toughest heart. It overlooks the majestic mountains of Timor-Leste with the famous Jesus statue looking over your shoulder. A decent Thai meal will cost roughly $5-$7 US dollars per plate. I tried the Chicken in Cashew Nuts ($5 US) with a nice Lychee Fruit Shake ($3 US). I followed the evening with several Bintang beers ($5 US) enjoying the ocean right in front of me. The restaurants grilled fish (priced at its catch size) is high on my list on things to do next. I have a passion for Thai food and having this restaurant in Dili is a life saver! Note: “Farang” dishes also available.
Little Pattaya restaurant in Dili has tables on the beach.
3) Kebab Club restaurant is located at the Rua Belarmino Lobo (Tel: +670-7297-121) close to the beach. If you are not looking closely it is very easy to miss. Try arriving at about 5pm when the grilled kebabs begin cooking. The meals have an authentic feel and its bread making is divine and special. Fresh baked breads on Tuesdays and Saturdays. I keep coming back for the Baklava! Some items can get pricey. Look at spending anywhere from $3 – $20 US dollars.
The Kebab Club restaurant in Dili.
4) Discovery Inn – DIYA Restaurant is located at Avenida Presidente Nicolau Lobato (Tel: +670-331-1111). This is the best and closes to luxury dining that you can get in Dili. It’s elegant and tropical feel entrance to Diya is quiet and welcoming. The restaurant is quite beautiful inside and the staff is neatly dressed and ready to assist. All speak English and make recommendations. I loved the meatballs, steaks, and pasta dishes. My heart remained at Diya for their home-made Molten Lava Chocolate Cake. It was heavenly! Now, don’t be surprised that you can walk out of this humble, luxury restaurant with a price tag of about $25-$30 US dollars per person for a dinner experience. If you find yourself in Dili with your special other on an anniversary, birthday, or just a nice romantic evening, this is the place to be.
Caz Bar restaurant in Dili.
5) Caz Bar restaurant is located at the heart of “White Beach” (Tel: +670-723-3961) past the Hera turn. During an early hike to the Statue of Jesus, I left this beautiful monument hungry and ready for some relaxing time. I walked a good 20 min. to finally reach the Caz Bar. My attention was captured by the number of foreigners sitting at this serene white beach enjoying the morning day – reading books, swimming, or simply just talking. Most of the expats make this a weekly weekend event. I took a table under a tree and ordered my breakfast. Delicious French styled Crepe with Nutella ($2.50 US) – yes Nutella in Dili, some cold Soda water, and a cup of coffee. I’ll be back next Saturday morning.
Caz Bar restaurant in Dili – foreigner beloved place.
6) Ocean Viewrestaurant is located at Bebonuk (Tel: +670-723-6041) on the Northern end of Dili. Are you in the mood for hardy Seafood? This is your place. The restaurant sports an awesome deck overlooking the ocean and bringing its seafood delights right to your table. I devoured the day’s special grilled Lobster ($20 US), fried Calamari for starters, and boiled Chinese dumplings. Yes, I know the dumplings were an odd combination but a delicious one! A Tiger Beer complimented the dinner and left me satisfied with this search. Thai food is also available!
Ocean view restaurant – seafood paradise.
So, that is my list of my top restaurants in Dili. I know I have left several others and welcome your input. My last comment is for those that need their fast food fix.
Eastern burger fast food restaurant in Dili.
7) Eastern Burgerfast food restaurant is located at the Avenida Presidente Nicolau Lobato just walking distance from the Discovery Inn and the famous ANZ Bank. The Eastern Burger caters to the town’s teenagers and young families on the weekend. This piece of American fast food inspired dishes carries a Beef Burger Combo to include drink and fries ($3.50 US), Egg Burger ($2 US), Hot Dog ($2.50 US) along with Asian styled fast food like Dumpling Noodle soup ($4.50 US) and Curry Chicken Rice Set ($5 US). Other oddities include Peanut Butter and Milk Set ($1 US) and even stranger is the French toast with cheese AND Peanut Butter ($3 US). The Eastern Burger restaurant packs a crowd. The food is fresh and served with a warm smile.
Eastern burger restaurant is visited by local kids and young families.
8) After your Eastern Burger bonanza, cross the street and find Dili’s ice cream shop –Que Bom.
Que Bom ice cream shop in Dili.
It’s only our first evening in Dili
DRUG APPROVALS BY DR ANTHONY MELVIN CRASTO .....FOR BLOG HOME CLICK HERE
Join me on twitter
Join me on google plus Googleplus
Googleplus
