Hydrochloric Acid → (3beta,20S)-pregn-5-ene-3,20-diol 20-acetate

Participants

Reaction Steps

iv)—A solution of (3β,20S)-3-[(1-ethoxyethyl)oxy]pregn-5-en-20-ol acetate (66.1 g) in acetone (1330 ml) was treated with a 4 M aqueous solution of hydrochloric acid (13.2 ml). The reaction mixture was stirred for 45 minutes and subsequently poured into a mixture of water (3 l) and a saturated aqueous solution of sodium hydrogen carbonate (500 ml). The resulting precipitate was collected by filtration and then dissolved in dichloromethane. The filtrate was extracted with ethyl acetate. The dichloromethane and ethyl acetate solutions were washed with a saturated aqueous solution of sodium hydrogen carbonate and with brine, dried over sodium sulfate, and concentrated under reduced pressure to give (3β,20S)-pregn-5-ene-3,20-diol 20-acetate (compound 5a; 53.5 g), which was used in the following step without further purification.

Provenance & Evidence