C([O-])(=[O:3])C.[K+].[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]1([C:17]([S:20][CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)([CH3:19])[CH3:18])[CH2:16][O:15]1.C1OCCOCCOCCOCCOCCOC1>O.CC(N(C)C)=O>[F:6][C:7]1[CH:12]=[C:11]([F:13])[CH:10]=[CH:9][C:8]=1[C:14]([OH:3])([C:17]([S:20][CH2:21][C:22]1[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=1)([CH3:19])[CH3:18])[CH2:16][OH:15]A solution of 1.12 g (11.4 mmol) of potassium acetate in 2 ml of water was added to a solution of 2.0 g (5.7 mmol) of (±)-2-(2,4-difluorophenyl)-2-(1-((4-methoxyphenyl)methylthio)-1-methylethyl)oxirane and 0.15 g (0.57 mmol) of 18-crown-6 in 12 ml of DMA, and the mixture was stirred at 110° C. for 30 hours. After being allowed to cool, 50 ml of water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was washed with a saturated sodium chloride aqueous solution, dried, and distilled under reduced pressure to remove the solvent. The residue was purified by column chromatography using a mixed solvent of hexane and ethyl acetate (5:1) as an eluent. The solvent was removed by distillation under reduced pressure, and the residue was recrystallized from a mixed solvent of isopropyl ether and diethyl ether to obtain 1.58 g (75%) of (±)-2-(2,4-difluorophenyl)-3-((4-methoxyphenyl)methylthio)- 3-methylbutane-1,2-diol as a colorless crystal.
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