Potassium Hydroxide → HCID 69625467, compound

Participants

Reaction Conditions

Reaction Steps

Potassium hydroxide (1.5 g, 27 mmol) and hydrazine monohydrate (3 ml, 62 mmol) were added to a suspension of (7α)-3,3-dimethoxy-7-methylestr-5(10)-en-17-one (1 g, 3 mmol) in 17 mL diethyleneglycol at room temperature under a nitrogen atmosphere. The reaction mixture was heated for 1 hour at 130° C. followed by 1 hour and 15 minutes at 230° C. A Dean-Stark trap was used to remove the water and the excess of hydrazine. The reaction mixture was cooled down to room temperature and water was added and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated to dryness to give the crude product (7α)-3,3-dimethoxy-7-methylestr-5(10)-ene, which was converted into (7α,16α,17β)-7,16-dimethyl-3-methylene-17-(1-propynyl)estr-5(10)-en-17-ol according to the procedures described above, mp 57° C.

Provenance & Evidence