p-Toluenesulfonic acid → HCID 86738866, compound

Participants

Reaction Steps

p-TSA (20 mg) is added to THF (5 ml) containing 17α-ethynyl-6-fluoro-17β-hydroxyandrost-5,9(11)-diene-3-one (VI, Example 5, 200 mg). After one hour at 20°-25°, the mixture is heated to reflux for 1.5 hrs. After cooling, the organic diluent is removed under reduced pressure. The residue is taken up in ethyl acetate, washed with aqueous sodium carbonate, the organic mixtures dried over sodium sulfate, and the organic diluent is removed under reduced pressure to give a solid. Filtration chromatography on silica dioxide (4 g), eluting with methylene chloride with increasing amounts of ethyl acetate, gives the title compound. Rf (ethyl acetate/hexane, 1/1)=0.7; NMR (CDCl3 +CD3OD) 0.8, 1.4, 2.6, 5.3, 5.7 and 6.1 δ.

Provenance & Evidence