Hydrochloric Acid → 9-Hydroxypregn-4-ene-3,20-dione

Participants

Reaction Steps

A solution of 20-isocyano-3,3-ethylenedioxypregna-5,17(20)-dien-9α-ol (2.30 g) in a mixture of tetrahydrofuran (60 ml) and aqueous 2N hydrochloric acid (20 ml) was refluxed for 1 hour. The reaction mixture was cooled to room temperature after which water (25 ml) and diethyl ether (100 ml) were added. The mixture was neutralised with IN sodium hydroxide solution. After separating the layers the aqueous phase was extracted twice with diethyl ether (50 ml). The combined organic layers were dried (MgSO4) and concentrated under reduced pressure to afford 2.02 g of the title compound.

Provenance & Evidence