Tetrahydrofuran → HCID 12135229, compound

Participants

Reaction Steps

Methyltriphenylphosphonium bromide (4.21 g, 11.8 mmol) was added to a stirred solution of potassium t-butoxide (1.26 g, 11.2 mmol) in 20 ml dry THF under a nitrogen atmosphere. The yellow suspension was stirred for 45 minutes at room temperature. A solution of (7α,17β)-7-methyl-3-keto-estr-5(10)-en-17-ol (3.4 g, 11.8 mmol) in 25 ml dry THF was added rapidly to the suspension. The yellow reaction mixture was stirred for 30 minutes at room temperature, poured on ice-water and extracted with ethyl acetate. The organic layer was washed with water, dried (Na2SO4) and evaporated to dryness to give 5.3 g of the title compound as a yellow oil. Column chromatography using toluene/ethyl acetate 95/5 (v/v %) as eluent gave 2.3 g of a colorless oil. Crystallization using heptane/petroleum ether gave (7α,17β)-7-methyl-3-methyleneestr-5(10)-en-17-ol (1.47 g, 44%) as a white solid, mp 111.8° C.

Provenance & Evidence