[F:1][CH2:2][C:3]([CH2:7][F:8])([OH:6])[C:4]#[CH:5].[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15](Cl)(=[O:17])=[O:16])=[CH:11][CH:10]=1.[H-].[Na+].O>O1CCCC1>[C:9]1([CH3:19])[CH:14]=[CH:13][C:12]([S:15]([O:6][C:3]([CH2:7][F:8])([C:4]#[CH:5])[CH2:2][F:1])(=[O:17])=[O:16])=[CH:11][CH:10]=1
An amount (6.6 g) of 1-fluoro-2-fluoromethyl-3-butyn-2-ol and p-toluenesulfonyl chloride (9.5 g) were dissolved in tetrahydrofuran (100 ml); to the solution under cooling with ice, 60% oily sodium hydride (2.4 g) was added under a nitrogen atmosphere. After the end of the addition, 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; hexane/methylene chloride=1/1) to give the titled compound (11.1 g).
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