HCID 19939313, compound → HCID 19939317, compound

Participants

Reaction Steps

To a stirred solution of 4,4-difluoro-3-difluoromethyl-3-hydroxy-1-(4-phenylsulfonylphenyl)but-1-yne (555 mg, 1.49 mmol) in tetrahydrofuran (15 mL) was added LAH (65 mg, 1.71 mmol) in one portion and the mixture was allowed to stir for 18 hours. The reaction was quenched with Na2SO4.10H2O, filtered and evaporated. The resulting material was purified by chromatography, with diethyl ether:hexanes (60:40) as the eluent, followed by chromatography, with diethyl ether:hexanes (50:50) as the eluent. The resulting material was recrystalized from methyl tert-butylether:hexanes to give the title compound; mp 123.0°-123.5° C.; NMR (CDCl3): 7.93-7.88 (m,4, Ar), 7.59-7.47 (m,5, Ar), 7.03 (d,1, J=16.2, vinylic), 6.33 (d,1, J=16.2, vinylic), 5.89 (t,2, J=54.8, CF2H), 3.02 (s,1, OH); MS: m/z=375(M+1). Analysis for C17H14F4O3S: Calculated: C, 54.54; H, 3.77; Found: C, 54.30; H, 3.84.

Provenance & Evidence