Dehydroepiandrosterone → 7-Oxodehydroepiandrosterone 3-acetate

Participants

Reaction Conditions

Reaction Steps

DHEA-Ac (1.1 gm., 0.0033 mol.) was dissolved in a mixture of ethyl acetate (10 ml) and tert-butyl hydroperoxide (70% aqueous solution from Aldrich, 2.0 ml, 0.015 mol). The mixture was stirred at 10° C. and solid calcium hypochlorite (0.65 gm.) was added in small portions during a period of seven hours. The aqueous layer was then separated and the organic layer was stirred with sodium sulfite solution (3.0 gm in 10 ml of water) for 3 hours at 40-45° C. and filtered over celite. The aqueous yellow layer was removed and the organic layer was washed with half saturated brine, dried over anhydrous magnesium sulfate, and the solvent was evaporated on a rotary evaporator. The crude product, crystallized from methanol, afforded 3β-acetoxyandrost-5-en-7,17-dione (3) as a white solid, weight 0.42 gm.

Provenance & Evidence