Water → 21-Acetylthiomethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Participants

Reaction Steps

3α-Hydroxy-21-methylene-5α-pregnane-11,20-dione (300 mg) was dissolved in thioacetic acid (2 ml) and left at room temperature for 3 hours. The mixture was poured into water and the precipitated oil extracted into ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and water, dried over anhydrous sodium sulphate, evaporated to a pale yellow foam and purified by preparative t.l.c. in ethyl acetate/petrol (1:1). The main band gave title compound (150 mg) as an off-white foam. [α]D + 60.5° (c 0.98).

Provenance & Evidence