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Saturday 31 March 2018

4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane

Image result for 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane

4,4,5,5-tetramethyl-2-phenethyl-1,3,2-dioxaborolane


http://orgsyn.org/demo.aspx?prep=v94p0234




 4,4,5,5-Tetramethyl-2-phenethyl-1,3,2-dioxaborolane (1) has the following physical and spectroscopic properties: Rf = 0.47 (3:97, ethyl acetate:pentane), the checkers report the following values for 1: Rf = 0.09 (3:97 ethyl acetate:pentane); R= 0.52 (10% EtOAc in hexanes); Merck silica gel 60 F254 plate; mp 38-39 °C; 

1H NMR pdf(CDCl3, 400 MHz) δ: 1.18 (t, = 8.4 Hz, 2H), 1.26 (s, 12H), 2.79 (t, J = 8.0 Hz, 2H), 7.16-7.22 (m, 1H), 7.23-7.32 (m, 4H); 

13C NMR pdf(CDCl3, 151 MHz) d: 25.0, 30.1, 83.2, 125.6, 128.1, 128.3, 144.6 [N.B. the carbon attached to boron was not observed due to quadrupolar relaxation]; 

HRMS (ESI+) calculated for C14H22BO2+ = 233.1707, mass found = 233.1710; 

IR (film): 3026, 2978, 2929, 1372, 1318, 1139, 848, 755, 703 cm-1

Anal. calcd for C14H21BO2: C, 72.44; H, 9.12. Found: C, 72.18; H, 9.28. 








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Tuesday 27 March 2018

BRUSH UP YOUR NMR, 4-(3,5-Dichloropyridin-4-yl)morpholine

str1
3,5-Dichloro-4-morpholinopyridine
 
 5 as a light-orange solid.
 
1H NMR (CDCl3, 400 MHz): δ = 8.35 (2H, s), 3.84 (4H, m), 3.37 (4H, m);
 
13C NMR (CDCl3, 101 MHz): δ = 150.8, 149.3, 128.4, 67.4, 50.4;
 
HRMS–ESI+m/z [M + H]+ calcd for C9H11Cl2N2O+: 233.02429; found: 233.02446.
 
 
 
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.8b00009
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Clc2cncc(Cl)c2N1CCOCC1

Saturday 24 March 2018

METHYL 2-(ACETYLTHIO)ACETATE

ChemSpider 2D Image | Methyl 2-(methylthio)acetate | C4H8O2S

Methyl 2-(methylthio)acetate

  • Molecular FormulaC4H8O2S
  • Average mass120.170 Da
  • 16630-66-3
  • S-Methylthioglycolate

DOI: 10.1021/acs.oprd.7b00378
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Monday 19 March 2018

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Abstract Image
This paper demonstrates an efficient, mild, and chemoselective synthesis of various thioesters via a HOTf-catalyzed S-acetylation of aromatic and aliphatic thiols using isopropenyl acetate as a cheap and convenient acetylating agent. During our tests, we also investigated the differences between the activities of metal triflates and triflic acid as catalysts in the acetylation of thiols. Finally, the potential of our concept has been increased by the implementation of Nafion as a heterogeneous catalyst for S-acetylation of thiols.

S-Acetylation of Thiols Mediated by Triflic Acid: A Novel Route to Thioesters

Faculty of ChemistryAdam Mickiewicz University in Poznańul. Umultowska 89b, 61-614 Poznań, Poland
Org. Process Res. Dev., Article ASAP
DOI: 10.1021/acs.oprd.7b00378
Publication Date (Web): March 12, 2018
Copyright © 2018 American Chemical Society
 
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Friday 9 March 2018

NEW DRUG APPROVALS HITS 20 LAKH VIEWS IN 218 COUNTRIES

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Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 
Green Chem., 2018, 20,973-977
DOI: 10.1039/C7GC03719H, Communication
Fuhong Xiao, Chao Liu, Dahan Wang, Huawen Huang, Guo-Jun Deng
A three starting material four component reaction (3SM-4CR) strategy is described to prepare [small beta]-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system.

Concise synthesis of ketoallyl sulfones through an iron-catalyzed sequential four-component assembly

 
Author affiliations

Abstract

A three starting material four component reaction (3SM-4CR) strategy is described to prepare β-acyl allylic sulfones from methyl ketones, sodium sulfinates and dimethylacetamide (DMA) in an iron-catalyzed oxidative system. In this process, DMA was used as a dual synthon to provide two carbons. A broad range of functional groups were tolerated in this reaction system.
 1-phenyl-2-(tosylmethyl)prop-2-en-1-one (3ab)
 
43.2 mg, 72% yield).
 
1 H NMR (400 MHz, CDCl3) δ 7.78 (d, J = 8.2 Hz, 2H), 7.68-7.65 (m, 2H), 7.55 (t, J = 7.4 Hz, 1H), 7.43 (t, J = 7.8 Hz, 2H), 7.30 (d, J = 8.3 Hz, 2H), 6.25 (s, 1H), 6.02 (s, 1H), 4.35 (s, 2H), 2.39 (s, 3H).
 
13C NMR (100 MHz, CDCl3) δ 194.7, 144.9, 136.1, 135.8, 135.7, 133.9, 132.6, 129.8, 129.6, 128.3, 128.2, 57.7, 21.6.
 
HRMS calcd. for: C17H17O3S+ [M+H]+ 301.08929, found 301.08908
 
STR1 STR2

1H NMR PREDICT




13C NMR PREDICT ABOVE

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Cc1ccc(cc1)S(=O)(=O)CC(=C)C(=O)c2ccccc2