Water → 4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

関与物質

反応手順

To a stirred solution of 1-(4-phenylsulfonylphenyl)-3-hydroxy-3-methyl-4,4,4-trifluorobut-1-yne (0.45 g, 1.27 mmol) in tetrahydrofuran (6 mL) was added lithium aluminum hydride (56 mg, 1.4 mmol) in one portion and the reaction mixture stirred for 18 hours. The reaction mixture was then treated sequentially with water (0.4 mL), 2N sodium hydroxide (0.4 mL), and water (1 mL). After 10 minutes of stirring the reaction was filtered through diatomaceous earth and the precipitate washed with ethyl acetate. The aqueous layer of the filtrate was separated and extracted further with ethyl acetate. The combined organic extracts were dried filtered, and evaporated. The crude oil was purified by chromatography, with chloroform:ethyl acetate as eluent (18:1), to yield the title compound as a white solid (0.17 g, 37%); mp 94°-97° C.; 250 MHz NMR (CDCl3): 1.56 (s,3, CH3), 2.30 (s,1, OH), 6.38 (d,1, J=16.0, vinylic), 6.89 (d,1, J=16.0, vinylic), 7.46-7.60 (m,5, Ar), 7.89-7.96 (m,4, Ar); MS (EI): m/z=356 (M+). Analysis for C17H15F3O3S: Calculated: C, 57.29; H, 4.24; Found: C, 57.24; H, 4.32.

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