Benzenesulfonyl chloride → 1-Fluoro-2-fluoromethyl-3-butyn-2-yl benzenesulfonate

Participants

Reaction Steps

An amount (1.2 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol and benzenesulfonyl chloride (1.8 g) were dissolved in tetrahydrofuran (10 ml); to the solution under cooling with ice, 60% oily sodium hydride (0.48 g) was added in a nitrogen atmosphere. After the end of the addition, the mixture was stirred for 4 hours while its temperature was raised to room temperature. A hexane/ether mixed solvent (1/1) was added to the reaction mixture, which was then 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; hexane/methylene chloride=1/1) to give the titled compound (2.2 g).

Provenance & Evidence