Ammonia → HCID 69916213, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (7α,17β)-7-ethyl-17-hydroxyestra-4,14-dien-3-one (Example 1a; 0.67 g) in dry tetrahydrofuran (13 ml) was added to a refluxing solution of lithium (0.31 g) in liquid ammonia (44 ml). After 30 min. stirring at −40° C., solid ammonium chloride was added and the ammonia was allowed to evaporate. Water was added and the product was extracted into ethyl acetate. The combined organic phases were washed with a saturated aqueous solution of ammonium chloride and brine, dried over sodium sulfate and concentrated under reduced pressure. Column chromatography afforded (5α,7α,17β)-7-ethyl-17-hydroxyestr-14-en-3-one (0.21 g), 1H-NMR (CDCl3) δ 5.02 (s, 1H), 3.98 (t, 1H, J=8.4 Hz), 0.99 (s, 3H), 0.89 (t, 3H, J=7.5 Hz).

Provenance & Evidence