Chloranil → 19-Hydroxy-4,6-androstadiene-3,17-dione

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Reaction Steps

19-Hydroxy-4-androstene-3,17-dione and chloranil are dissolved in t-butanol which is rapidly brought to its reflux temperature. The t-butanol is removed by distillation at atmospheric pressure at such a rate that the reflux time and distillation time approximate one hour. The dark pasty residue is triturated with hot chloroform and cooled. The solid residue is removed by filtration and the filtrate extracted with water, followed by a 2% sodium hydroxide solution, washed with water, dried over magnesium sulfate and the solvent removed under vacuum to yield 19-hydroxy-4,6-androstadiene-3,17-dione. The diene so obtained is dissolved in acetone and chilled in an ice bath. Jones reagent is added over a period of 10 minutes and stirring continued for an additional 45 minutes. The mixture is poured onto water. The solid which separates is filtered and recrystallized from benzene to yield 4,6-androstadiene-3,17,19-trione.

Provenance & Evidence