Iodine → HCID 131724404, compound

Participants

Reaction Steps

Iodine (1.27 g, 5 mmol) and 19-nor-4-androstene-3,17-dione (272 mg, 1 mmol) were dissolved in methanol (15 mL), and the resultant mixture was stirred for two hours under cooling in an ice-bath. The temperature of the mixture was maintained at room temperature, and the mixture was further stirred for 1.5 hours, and subsequently, refluxed for one hour. The reaction mixture was cooled to room temperature, and an aqueous solution of sodium thiosulfate was added to the mixture. The mixture was extracted with chloroform, and the organic phase was washed sequentially with an aqueous solution of sodium bicarbonate and saturated brine. The washed matter was dried over magnesium sulfate anhydrate, filtered, and evaporated under reduced pressure. The residue was purified through silica gel column chromatography (chloroform), to thereby yield 220 mg of the title compound (yield: 74%).

Provenance & Evidence