Methyl iodide → HCID 12135245, compound

Participants

Reaction Conditions

Reaction Steps

A solution of (7α)-3,3-dimethoxy-7-methylestr-5(10)-en-17-one (1.5 g, 4.5 mmol) and 1,3-dimethyl-3,4,5,6-tetrahydro-2(1H)-pyrimidinone (DMPU, 1.2 mL, 9.9 mmol) in 30 mL dist. THF was added in approx. 8 minutes to a stirred solution of lithium bis(trimethylsilyl)amide (LiHMDS, 4.96 mL, 1M in THF) in 15 mL distillated THF at −40° C. under a nitrogen atmosphere. The reaction mixture was stirred for 45 minutes at −40° C. A solution of iodomethane (730 μL, 11.7 mmol) in 1 mL dist. THF was added and stirred for 1 hour and the temperature was allowed to warm up to 0° C. Water and sat. ammonium chloride solution were added and extracted with ethyl acetate. The organic layer was washed with brine, dried (Na2SO4) and evaporated to dryness. Column Chromatography using heptane/ethyl acetate 95/5 (v/v %) as eluent gave (7α,16α)-3,3-dimethoxy-7,16-dimethylestr-5(10)-en-17-one (990 mg, yield 65%).

Provenance & Evidence