Ammonium Chloride → HCID 69529940, compound

Participants

Reaction Steps

2.43 g (5.37 mmol) of 3-methoxy-17-tosylhydrazono-13α-estra-1,3,5(10)-triene is suspended in 20 ml of anhydrous methyl-tert-butylether. 1.61 ml of a 10 M n-butyllithium solution in hexane is slowly added in drops to this suspension. It is stirred for 1 hour at room temperature. While being cooled, 50 ml of saturated ammonium chloride solution is added in drops. After the organic phase is separated, it is extracted with ethyl acetate. The combined organic phases are washed with water and saturated sodium chloride solution and dried (MgSO4). The crude product (2.1 g of brown oil) is chromatographed on silica gel, whereby 0.81 g of 3-methoxy-13α-estra-1,3,5(10),16-tetraene is obtained as a colorless oil; [α]D=−6° (chloroform; c=0.94).

Provenance & Evidence