Thiophenol → (-)-3-t-Butyldimethylsilyloxybutyric acid phenylthioester

Participants

Reaction Steps

To a solution of 3.18 g (19.2 mmol) of (-)-3-t-butyldimethylsilyloxybutyric acid and 2.26 ml (22 mmol) of thiophenol dissolved in 100 ml of methylene chloride, 4.53 g (22 mmol) of N,N'-dicyclohexylcarbodiimide was added. After stirring the mixture at room temperature for 2 hours, the resultant was filtered and the filtrate was concentrated and distilled (110° to 116° C./0.3 mmHg) to give 5.00 g of (-)-3-t-butyldimethylsilyloxybutyric acid phenylthio ester (yield: 83%).

Provenance & Evidence