Dimethyl Carbonate → HCID 86760340, compound

Participants

Reaction Steps

A solution of 3-benzyloxy-1,3,5(10)-estratrien-17-one (2) (4.00 g, 11.1 mmol) in dry THF (5 mL) was added over a period of 30 min to a solution of dimethylcarbonate (2.34 mL, 27.8 mmol) and potassium hydride (1.42 g, 34.7 mmol) in dry THF (40 mL). Then, the mixture was heated to reflux for a period of 3 h. Most of the solvent was then evaporated and the residue was diluted with ethyl acetate (100 mL) and treated with a saturated ammonium chloride solution (50 mL). The organic phase was washed with water (6×40 mL), dried and evaporated to give a yellowish solid. Trituration of the residue with a mixture of acetone:hexanes (1:1) yielded the title compound in 90% yield as a white solid.

Provenance & Evidence