Iodine → HCID 131724404, compound

Participants

Reaction Steps

Iodine (7.01 g, 27.6 mmol), 19-nor-4-androstene-3,17-dione (5.00 g, 18.4 mmol), and ceric ammonium nitrate (15.1 g, 27.6 mmol) were dissolved in methanol (150 mL), and the resultant mixture was refluxed for two hours. The resultant 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 subjected to a separation-purification step through silica gel column chromatography (chloroform), to thereby yield 2.20 g of the title compound (yield: 40%) and, as a by-product, 2.45 g of estrone-methyl ether (yield: 47%).

Provenance & Evidence