Methyl trifluoromethyl ketone → 1,1,1-Trifluoro-2-methyl-3-(4-phenylsulfonylphenylthio)propan-2-ol

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Reaction Steps

Potassium hydroxide (0.129 g, 2.3 mmol) in water (2 mL) was added dropwise to a stirred suspension of trimethylsulfoxonium iodide (0.476 g, 2.2 mmol), trifluoroacetone (0.258 g, 2.3 mmol) in dichloromethane (5 mL) under nitrogen at 0° C. The mixture was stirred for 0.5 hours and was then refluxed for a further 0.5 hour. After cooling to room temperature a solution of 4-(phenylsulfonyl)thiophenol (0.5 g, 2 mmol), potassium hydroxide (0.112 g, 2 mmol), and water (5 mL) was added in one portion and the mixture was stirred for 2 hours. The reaction mixture was diluted with dichloromethane, washed (saturated aqueous ammonium chloride solution, water, brine), and dried (Na2SO4). Evaporation gave an oil that crystallized from ether/ethyl acetate/hexane to give a white solid. The filtrate was evaporated to give a solid which was recrystallized from ether/hexane to give the title compound (0.24 g); mp 100°-102° C.; NMR: 1.35 (s,3 , CH3), 3.35 (m,2, SCH2), 6.41 (s,1, OH), 7.57 (d,2, J=9, Ar), 7.67 (m,3, Ar), 7.83 (d,2, J=8.7, Ar), 7.94 (d,2, J=6.9, Ar). MS: m/z=377 (M+1). Analysis for C16H15F3O3S2 : Calculated: C, 51.06; H, 4.02; Found: C, 51.50: H, 3.94.

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