Boron trifluoride etherate → HCID 12134980, compound

Participants

Reaction Steps

To a suspension of the known 3-hydroxy-4-methylestra-1,3,5(10)-trien-17-one (ref. Kaneko et al., 1964; Chemical Abstracts Registry Number [68969-90-4], 30 mg, 0.11 mmol) in 1 mL of anhydrous pentane and 0.5 mL of t-butanol, was added 0.03 mL of boron trifluoride diethyl etherate while cooling with an ice bath and stirring. After 20 min., the reaction was stirred at room temperature for 2.5 h. Ice was added and the solid that formed was filtered, washed with water and dried overnight in a vacuum desiccator. The crude product was purified by chromatography (silica gel eluted with 10% ethyl acetate in hexanes) and then recrystallized from methylene chloride-hexanes to give 20 mg of pure product (56% yield): m.p. 190-192° C.; 1H NMR(CDCl3) δ0.90 (s, 3H, CH3), 1.42 (s, 9H, C(CH3)3), 2.13 (s, 3H, CH3), 2.79-2.81 (m, 2H, CH2), 7.16 (s, 1H, Ar—H); 13C NMR (CDCl3) δ 11.06, 13.70, 21.44, 26.16, 26.60, 26.68, 27.54, 29.82 (3×C), 31.55, 34.43, 35.84, 37.63, 44.52, 47.89, 50.34, 121.42, 131.28, 133.00, 133.55, 150.56, 221.45. (Anal. calc'd. for C23H32O2: C, 81.13; H, 81.09. Found: C, 81.09; H, 9.59.)

Provenance & Evidence