Acetic Acid → 3-Methoxyestra-1,3,5(10),8-tetraen-17beta-ol

Participants

Reaction Steps

Add sodium borohydride (0.5 g.) in ethanol (60 cc.) with stirring to 13-methyl-3-methoxygona-1,3,5(10),8-tetraen-17-one (2.0 g.) in ethanol (150 cc.) at 14°-15°. Leave the mixture at room temperature for 1 hour, acidify with glacial acetic acid and evaporate to dryness under reduced pressure. Treat the residue with water, ether-extract and wash and dry. Evaporate the extracts. Recrystallize the residue from a mixture of methanol (15 cc.) and water (3 cc.) to obtain the title product (0.90 g.), m.p. 110°-2°. A sample sublimes at 110°/10-4 mm. and has an ultra-violet absorption peak at 277 mμ (ε 14,500).

Provenance & Evidence