Bis[alpha,alpha-bis(trifluoromethyl)benzenemethanolato]diphenylsulfur → 3beta-Benzoyloxy-14alpha-cyano-4,4-dimethyl-5alpha-cholest-6-ene

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Reaction Steps

To a solution of 3β-benzoyloxy-14α-cyano-4,4-di-methyl-5α-cholestan-7-ol (100 mg, 0.18 mmole) prepared as in Example 13(iv), in dichloromethane (2.5 mL) held at -78° C. was added Martin sulfurane dehydrating agent (bis [α,α-bis(trifluoromethyl)benzenemethanolato]-diphenyl-sulfur) (240 mg, 0.36 mmole) in dichloromethane (2.5 mL). The mixture was warmed to ambient temperature, stirred for an additional 6 hours, concentrated in vacuo and the residue was triturated with methanol to give 3β-benzoyloxy-14α-cyano-4,4-dimethyl-5α-cholest-6-ene (80 mg, 82%); mp 232°-233° C. (from CH2Cl2/MeOH).

Provenance & Evidence