Diethyl Ether → 4,4,4-Trifluoro-3-hydroxy-3-fluoromethyl-1-(4-phenylsulfonylphenyl)but-1-yne

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Reaction Steps

To a cooled (-78° C.) solution of 4-phenylsulfonylphenylethyne (1.68 g) in anhydrous tetrahydrofuran (70 mL) was added n-butyl lithium (3.06 mL of a 2.5 M solution in hexanes). The solution was stirred for 15 minutes at -78° C. before 1,1,1,3-tetrafluoroacetone (2.96 mL of a 40% diethyl ether solution) was added. The reaction mixture was kept at -78° C. for five minutes before quenching with 2N hydrochloric acid. Diethyl ether was added and the aqueous layer extracted further with diethyl ether. The combined organic layers were dried, evaporated and the product purified by chromatography, with diethyl ether:chloroform (1:9) as eluent. This yielded the title compound as a white solid (1.64 g) mp 119-120.8; (300 MHz) (CDCl3): 3.77 (s,1, OH), 4.55-4.79 (m,2, CH2F), 7.48-7.61 (m,5, Ar), 7.86-7.94 (m,4, Ar); MS: m/z=373 (M+1). Analysis for C17H12F4O3S: Calculated: C, 54.84; H, 3.25; Found: C, 54.70; H, 3.37.

Provenance & Evidence