Lithium → HCID 68144569, compound

Participants

Reaction Steps

Add 13β-n-propyl-3-methoxy-gona-1,3,5(10), 8-tetraen-17β-ol (3.1 g.) dissolved in a mixture of tetrahydrofuran (10 cc.) and freshly distilled aniline (60 cc.) to liquid ammonia (160 cc.) and add lithium metal (1.5 g.) in small pieces. Stir the reaction mixture for 3 hours, then quench with solid ammonium chloride (12.5 g.) and take up in water. Ether-extract the product and evaporate the washed and dried extracts to obtain a semisolid residue of crude 13β-n-propyl-3-methoxy-gona-1,3,5(10) -trien-17β-ol (3.1 g.); ultraviolet absorption peak at 279 mμ (ε1,800).

Provenance & Evidence