Ammonia → HCID 86748619, compound

Participants

Reaction Steps

800 ml of ammonia is condensed at -70° C. and mixed with 1.39 g of lithium. After occurrence of the characteristic blue coloring, 18.6 g (40 mmol) of 17,17-bis-(ethylenedioxy)-11-(4-methoxyphenyl)-5,9(11)-estradiene dissolved in 400 ml of tetrahydrofuran is instilled. After 20 more minutes of stirring, the excess lithium is decomposed by the addition of water, the ammonia evaporates, the reaction mixture is poured on saturated ammonium chloride solution and the aqueous phase is extracted with ethyl acetate. The combined organic phases are washed with saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation in a vacuum. After chromatography of the crude product on silica gel with a mixture of ethyl acetate/hexane, 15.2 g of 3,3;17,17-bis-(ethylenedioxy)-11β-(4-methoxyphenyl)-5-estrene and 1.4 g of 17,17-bis-(ethylenedioxy)-11-(4-hydroxyphenyl)-5,9(11) -estradiene* are isolated as white foams.

Provenance & Evidence