Dimethylacetamide → 17alpha-Ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol

Participants

Reaction Steps

Add solid lithium acetylide-ethylenediamine complex (9.5 g) to 3-methoxyestra-1,3,5(10),8-tetraen-17-one (10 g) in dimethylacetamide (100 ml), stir the mixture for 15 hours and then pour into ice water. Extract with ether-benzene (1:1), and wash, dry and evaporate the organic extract. Recrystallize the residue from methanol to obtain dl-17α-ethynyl-3-methoxyestra-1,3,5(10),8-tetraen-17-ol (2.8 g), m.p. 133°-137°; infrared absorption peaks at 3.1 μ, 6.25 μ.

Provenance & Evidence