Ammonia → HCID 68143124, compound

Participants

Reaction Steps

To 13-n-butyl-3-methoxygona-1,3,5(10), 8-tetraen-17β-ol (0.8 g.) in aniline (20 cc.) and tetrahydrofuran (10 cc.) add liquid ammonia (100 cc.), followed by sodium (0.8 g.) in small pieces during 5 minutes while stirring the mixture. After a further 15 minutes stirring, discharge the blue color with solid ammonium chloride. Work up the product with ether in the usual way, and evaporate the resulting ether solution to leave as residue a gum; take this up in hot methanol (10 cc.), filter a little insoluble material and allow the solution to stand for 12 hours at 0° C. Crystals of 13-n-butyl-3-methoxygona-1,3,5(10)-trien-17β-ol are deposited and filtered off (0.6 g.), m.p. 123°-125° C after previous softening and a little melting at 60°-70° C.; ultraviolet absorption peak at 278 mμ (ε2,100); infrared absorption peaks at 2.86 -2.97 (broad band), 6.21, 7.94, 9.62 μ.

Provenance & Evidence