4-Bromoanisole → 6-Methoxy-10-(4-methoxy-phenyl)-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one

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Reaction Steps

Combine 6-methoxy-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (1.0 g, 4.3 mmol), 4-bromoanisole (0.81 g, 4.3 mmol), palladium acetate (49.0 mg, 0.218 mmol), t-butyl phosphine (0.133 g, 0.658 mmol), sodium t-butoxide (0.457 g, 4.7 mmol), tetrahydrofuran (38.0 mL), and stir under nitrogen atmosphere at 80° C. in a glass bomb. After 18 hours, quench reaction with acetic acid (5 mL) in a glove box and extract with ethyl acetate. Wash the ethyl acetate with sodium bicarbonate solution and then brine, dry over sodium sulfate, and concentrate in vacuo. Add diethyl ether and collect precipitate to yield the titled compound (0.78 g, 55%) as a white solid. TLC Rf=0.26 in 5:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 8.04 (d, 1H, J=8.8 Hz), 7.06 (d, 2H, J=8.4 Hz), 6.86 (m, 3H), 6.75 (m, 1H), 3.89 (m, 4H), 3.80 (s, 3H), 3.01 (m, 1H), 2.65 (m, 1H), 1.81 (m, 3H), 1.46 (m, 5H).

Provenance & Evidence