To a mixed suspension of (E)-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-ylidene)acetonitrile (10.0 g, 50.7 mmol) in toluene (37.5 mL) and methanol (12.5 mL) were added activated cobalt (7.22 g) and 14.4% aqueous solution of potassium hydroxide (1.4 g), and stirred for 6.5 hrs at to 50° C. under hydrogen atmosphere (0.2 MPa). The reaction solution was filtered, and to the filtrate were added toluene (170 ml) and methanol (35 ml) to separate the layers. 0.5N Hydrochloric acid (101 mL) was added to the organic layer, and stirred for 30 minutes at 25 to 30° C. Then, the layers were separated, and active charcoal (1 g) was added to the aqueous layer, followed by stirring. The active charcoal was removed by filtration to give an aqueous solution of title compound (246 g, Net 12.0 g, yield 99.6%).
http://www.google.com/patents/US20130079397
| (E)-2-(6,7-dihydro-1H-indeno[5,4-b]furan-8(2H)-ylidene)acetonitrile |
| CAS NO.: 196597-79-2 |
| Purity: 98.00% |
| Formula: C13H11NO |
| Molecular Weight: 197.24 |
| Product description： Intermediate of Ramelteon CAS#196597-26-9 |
To a solution of toluene (184 g), 1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-one (8.5 g, 48.9 mmol) and diethyl cyanomethylphosphonate (10.4 g, 58.7 mmol) was added dropwise 28% sodium methoxide solution in methanol (11.3 g) over 1 hr under ice-cooling, and reacted for 4 hrs. To the reaction solution was added dropwise water (85 μg), and warmed, then the layers were separated. The organic layer was washed with water, and filtered to remove dusts under pressurization. The organic layer was concentrated under reduced pressure, and to the residue was added methanol and concentrated under reduced pressure to substitute the solvent. After stirring for 1 hr under heating with reflux, the solution was cooled and matured for 1 hr. The crystallization solution was filtered, and the crystals were dried under reduced pressure to give title compound (amount 8.1 g, yield 84.4%).
