HCID 13145956, compound → HCID 22823201, compound

Participants

Reaction Steps

Potassium t-butoxide (as a 20% solution in THF, 1.6 ml) is added to THF (10 ml) containing 6α-fluoro-androst-4,9(11)-diene-3,17-dione (V, Example 4, 350 mg), previously cooled to -10°. After stirring at -10° for 40 min, acetylene is slowly bubbled in over 2 hrs. The solution is then allowed to warm to 20°-25°, quenched with aqueous ammonium chloride and extracted with ethyl acetate which is then back extracted with water, dried over sodium sulfate, the solvent removed under reduced pressure to give the title compound Rf (ethyl acetate/hexane, 1/1)=0.6; NMR (CDCl3 +CD3OD) 0.9, 1.4, 2.6 and 5.7 δ.

Provenance & Evidence