Acetic Acid → HCID 70626928, compound

Participants

Reaction Steps

A mixture of 1 part of 3β-{[(1,1-dimethylethyl)dimethylsilyl] oxy}-17β-[(4,4-dimethylpentyl)oxy]androst-5-en-7-one, 22 parts of tetrahydrofuran, 10 parts of acetic acid, and 5 parts of water is heated at approximately 60° under reflux for 48 hours, then poured into 200 parts of water. Approximately 15 parts of sodium chloride is stirred into the resultant mixture. The solid which precipitates is isolated by filtration, washed on the filter with water, dried in air, and finally taken up in 1,1'-oxybisethane. Solvent is thereupon removed by vacuum distillation; and the residue is chromatographed on silicic acid, using benzene and mixtures thereof with increasing amounts of ethyl acetate as developing solvent. Eluates are selected via thin layer chromatography which, upon evaporation of solvent and recrystallization of the residues from a mixture of 2-propanone and hexane, afford 3β-hydroxy-17β-[(4,4-dimethylpentyl)oxy]androst-5-en-7-one melting at 203°-205°. The product has the formula ##STR10##

Provenance & Evidence