Androsta-1,4-diene-3,17-dione → 1,5-Androstadiene-3,17-dione

Participants

Reaction Steps

To a solution of potassium t-butoxide in dimethylsulfoxide at 25° under nitrogen is added 1,4-androstadiene-3,17-dione in dimethylsulfoxide with stirring. After 15 minutes the mixture is poured onto cold aqueous ammonium chloride. The solid which forms is rapidly filtered, washed well with water and dissolved in ether. The ether solution is washed with water, dried over sodium sulfate and evaporated at room temperature to yield 1,5-androstadiene-3,17-dione.

Provenance & Evidence