Ammonia → HCID 53821585, compound

Participants

Reaction Steps

Add 13β-n-butyl-3-methoxy-gona-1,3,5(10)-trien-17β-ol (0.5 g.) in a mixture of tetrahydrofuran (5 cc.) and ether (15 cc.) dropwise to a stirred solution of lithium (0.5 g.) in liquid ammonia (60 cc.). After 5 minutes beyond completion of addition, add ethanol (8 cc.) dropwise and when the blue color is discharged, add water and extract the mixture with ether. Work up in the usual way to give 13β-n-butyl-3-methoxy-gona-2,5(10)-dien-17β-ol as a crystalline solid, m.p. 135°-9°; infrared absorption peaks at 2.97, 6.25, 6.38 and 8.16 μ.

Provenance & Evidence