Acetone → 19-Methylthioandrost-4-ene-3alpha,17beta-diol

Participants

Reaction Steps

0.6 g of NaBH4 was added to a solution of 6 g of 19-methylthioandrost-4-ene-3,17-dione in a mixture of 25 ml of THF and 25 ml of methanol. After 1/2 hour, 2 ml of acetone, followed by 5 ml of 50% acetic acid were added. After stirring for 1/2 hour, the mixture was poured out into 200 ml of 5% NaHCO3 solution. Subsequently, the product was extracted with CH2Cl2. After washing, drying and evaporating down the organic layer, the residue obtained was chromatographed using silica gel. In this manner, 4.8 g of 19-methylthioandrost-4-ene-3α,17β-diol were obtained, melting point 85°-87° C., (Rf =0.23 (toluene/ethyl acetate 7:3).

Provenance & Evidence