Chloranil → HCID 86734740, compound

Participants

Reaction Steps

17β,19-Dihydroxy-4-androsten-3-one diacetate and chloranil are dissolved in t-butanol which is rapidly brought to reflux. The t-butanol is distilled at atmospheric pressure at such a rate that the total reflux and distillation time equals one hour. The dark residue which remains is triturated with hot chloroform and filtered. The filtrate is extracted with water, a 2% sodium hydroxide solution and again with water. The organic layer is dried over magnesium sulfate and the solvent removed to yield 17β,19-dihydroxy-4,6-androstadien-3-one diacetate. The diene so prepared is refluxed with dichlorodicyanobenzoquinone in anhydrous dioxane for a period of about 48 hours. The mixture is cooled, filtered and the filtrate poured onto a mixture of methylenechloride and water. The organic layer is separated, washed with water, dried well over magnesium sulfate and the solvent removed. The dark residue remaining is chromatographed on silica gel and eluted with methylenechloride to yield from the eluate the desired 17β,19-dihydroxy-1,4,6-androstatrien-3-one diacetate.

Provenance & Evidence