Water → 1-Fluoro-2-fluoromethyl-3-butyn-2-yl propanesulfonate

Participants

Reaction Steps

An amount (2.4 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol was dissolved in tetrahydrofuran (20 ml); to the solution under cooling with ice, 60% oily sodium hydride (0.96 g) was added under a nitrogen atmosphere. After stirring for 30 minutes under cooling with ice, propanesulfonyl chloride (2.2 ml) was added dropwise. The mixture was stirred for 5 hours while its temperature was raised to room temperature. Water was added to the reaction mixture, followed by extraction with ether. The extract was washed with water and a saturated aqueous solution of sodium chloride, dried with anhydrous sodium sulfate and concentrated under reduced pressure. The resulting residue was subjected to silica gel column chromatography (eluent; 30% ethyl acetate/hexane) to give the titled compound (4.1 g).

Provenance & Evidence