Sodium hydride → (S)-(-)-4,4,4-Trifluoro-3-hydroxy-3-methyl-1-(4-phenylsulfonylphenyl)-trans-but-1-ene

Participants

Reaction Conditions

Reaction Steps

To a tetrahydrofuran (5 mL) solution of (2S)-1,1,1-trifluoro-2-methyl-4-(4-phenylsulfonylphenyl)-2,3-butanediol (product described in Example 13.d.) (500 mg, 1.34 mmol) was added sodium hydride (60 mg, 60% at dispersion, 1.57 mmol). The mixture was heated to 65° C. After 10 minutes, another aliquot of sodium hydride (60 mg, 60% oil dispersion, 1.57 mmol) was added. The mixture was heated to reflux (66° C. internal temp.) for 1.5 hours, after which time a third aliquot of sodium hydride (40 mg, 60% oil dispersion, 1.04 mmol) was added. The reaction was heated to reflux for 2.0 additional hours, then cooled to ambient temperature and stirred for an additional 1.6 hours. The reaction was quenched with water and the product extracted into diethyl ether. The organic extracts were dried and evaporated. The crude product was purified by chromatography, with diethyl ether:dichloromethane as the eluent (gradient, 0:100 to 2:98) to give the title compound as a white solid (326 mg, 68%). See Example 13 for characterization data.

Provenance & Evidence