Potassium Hydroxide → 3beta-Hydroxy-5alpha-pregn-16-ene-11,20-dione

Participants

Reaction Steps

A solution of 3β-acetoxy-5α-pregn-16-ene-11,20-dione (25.7 g.) in dioxan (500 ml.) was treated with potassium hydroxide (10 g.) and water (250 ml.) and the mixture allowed to stand at room temperature for 1 hour. After a further 1 hour at 40° the mixture was diluted with water and the product filtered off. The crude material was dissolved in chloroform and filtered through a column of grade III neutral alumina. Crystallisation from acetone-petrol gave pure 3β-hydroxy-5α-pregn-16-ene-11,20-dione (17.65 g.) as small plates m.p. 217.5°, [α]D + 82.9°. (c 1.1)

Provenance & Evidence