Hydrochloric Acid → 3alpha-Toluene-p-sulphonyloxy-5alpha-pregnan-20-one

Participants

Reaction Steps

3α-Hydroxy-5α-pregnan-20-one (5.12 g) in pyridine (40 mL) was treated with toluene-p-sulphonyl chloride (5.6 g) , and the reaction mixture was stirred at room temperature for 18.0 h. This solution was poured into dilute (5%) hydrochloric acid (200 mL) and washed three times with chloroform (150 mL portions). The combined organic phase was extracted with more 5% hydrochloric acid and water, dried over magnesium sulfate and evaporated to an oil which on standing crystallized and gave 3α-toluene-p-sulphonyloxy-5α-pregnan-20-one as a white solid.

Provenance & Evidence