Oxiranecarboxylic acid, 3-phenyl-, ethyl ester, trans- synthesis
- Product Name:Oxiranecarboxylic acid, 3-phenyl-, ethyl ester, trans-
- CAS Number:2272-55-1
- Molecular formula:C11H12O3
- Molecular Weight:192.21
Yield:96 % de
Reaction Conditions:
with 2-(trimethylsilyl)phenyl trifluoromethanesulfonate;cesium fluoride in acetonitrile at 60; for 24 h;Sealed tube;Darzens Condensation;
Steps:
8 General procedure for synthesis of epoxide 3
General procedure: A mixture of amine 1 (46.4mg, 0.24mmol), 2-(trimethylsilyl)phenyl triflate (89.5mg, 0.30mmol), CsF (91.1mg, 0.60mmol), and acetonitrile (0.80mL) in a sealed tube was heated at 60°C (oil bath) for 10 min, and a solution of aldehyde 2 (0.20mmol) in acetonitrile (0.40mL) was added. The mixture was stirred at 60°C for 24h, cooled to room temperature, and purified by silica gel chromatography, eluting with ethyl acetate/petroleum ether (1:10 v/v), to give epoxide 3.
References:
Xu, Ya-Nan;Tian, Shi-Kai [Tetrahedron,2019,vol. 75,# 12,p. 1632 - 1638]
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