Potassium Carbonate → HCID 70520810, compound

Participants

Reaction Steps

To a solution of 2.9 ml of liquid hydrogen fluoride and 2.0 ml of THF previously cooled to -78° under nitrogen is added a solution of 17b-difluoroandrosta-4,9(11)-dien-3-one (XI, Example 5, 1.5 g) with 10-15 ml of methylene chloride. After termal equilibrium is obtained, solid N-chlorosuccinimide (0.8 g) is added and the mixture stirred at -78° for approximately 3 hrs. The mixture is warmed to -20° over a 25 min period and then warmed to 0° over the next 30 min and then poured slowly into an ice-cooled solution of potassium carbonate (15 g) and water (50 ml). The phases are separated and the aqueous phase is washed twice with methylene chloride. The organic phases are combined and washed with a solution of sodium sulfite (2.5 g in 30 ml), dried over sodium sulfate and concentrated under reduced pressure to give a solid which is purified by column chromatography to give the title compound.

Provenance & Evidence