Stimovul,Organon,W. Germany,1976
Reduction of 16-keto-17(α)-hydroxyestratrienol-3-methyl to 16,17-
dihydroxyestratrienol-3-methyl ether: A solution of 800 mg of the alpha ketol
methyl ether in 100 cc of ethanol and 10 cc of acetic acid was carefully
maintained at 40°C (water bath), and 200 g of freshly prepared sodium
amalgam (2%) were added in small pieces with efficient swirling. Before all ofthe amalgam had been added, a precipitation of sodium acetate occurred, and
at this point an additional 100 cc of 50% acetic acid were added. After all the
reducing agent had been added, the mixture was transferred to a separatory
funnel with ether and water. The mercury plus aqueous phase was separated,
after partitioning, from the ether; the latter may be further washed with
water, with 0.5N sodium hydroxide, and again with water to purify the alpha
glycol. Evaporation of the ethereal phase yielded a crystalline residue of the
isomeric transoid (16(β),17(α)-dihydroxy-steroid-3-methyl ether and cisoid
16(α),17(α)dihydroxy-steroid-3-methyl ether.
