Hydrochloric Acid → HCID 10050846, compound

Participants

Reaction Conditions

Reaction Steps

A 1.6 M solution of n-BuLi (17.5 mL) in hexanes was added dropwise by syringe under argon atmosphere at -78° C. to a solution of estradiol (4) (5.88 g, 11.2 mmol) in anhydrous THF (150 mL), and the resulting reaction mixture was stirred at -78° C. for 2 h. Anhydrous DMF (5.5 mL) was added and the stirring was continued for 1 h at -78° C. The mixture was warmed to 0° C. and stirred for 1 h, and poured onto an ice-cold solution of 3N HCl (100 mL). The aqueous layer was extracted with ether (3×300 mL). The combined organic layer was washed with 50% brine-water (100 mL), brine (150 mL), and dried over anhydrous sodium sulfate. The organic layer was filtered and evaporated under reduced pressure to afford impure estradiol (2), which was purified over a silica gel column using hexane-ethyl acetate as eluant. Appropriate fractions were combined and evaporated under reduced pressure to afford estradiol (2) (4.36 g, 82%): mp 145-147° C.; IR (KBr) 2920, 2820, 1675, 1600, 728, 685 cm-1, 1H NMR (CDCl3) δ 0.88 (s, 3 H), 1.1-2.5 (m, 13 H), 2.80-2.97 (m, 2 H), 3.50 (t, J=8.5 Hz, 1 H), 4.56 (s, 2 H), 5.65 (s, 2 H), 6.75 (s, 1H), 7.20-7.50 (m, 10 H), 7.78 (s, 1 H), 10.5 (s, 1 H). Anal. (C34H40O3)C,H.

Provenance & Evidence