Tetrahydrofuran → 3-Hydroxy-17-[(4-methylpentyl)oxy]androst-5-en-7-one

Participants

Reaction Steps

A mixture of 3 parts of 3β-{(1,1-dimethylethyl)dimethylsilyl] oxy}-17β-[(4-methylpentyl)oxy]androst-5-en-7-one, 45 parts of tetrahydrofuran, 15 parts of acid, and 10 parts of water is heated at approximately 60° for 48 hours, whereupon 300 parts of water is added and the resultant mixture is extracted with 1,1'-oxybisethane. The extract is washed with aqueous 5% potassium bicarbonate, dried over magnesium sulfate, and strippd of solvent by vacuum distillation. The residue is chromatographed on silica gel, using mixtures of benzene and ethyl actate (initially comprising 10% ethyl acetate and progressively increasing the proportions thereof to 25%) as developing solvent. Eluates are selected via thin layer chromatography which, upon evaporation of solvent and recrystallization of the residues from a mixture of 1,1'-oxybisethane and hexane, afford 3β-hydroxy-17β-[(4-methylpentyl)oxy]androst-5en-7-one melting at approximately 133.5°-134.5°. The product has the formula ##STR8##

Provenance & Evidence