Ethanol → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ol

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Reaction Steps

Combine 6-methoxy-10-(4-methoxy-phenyl)-2,3,4,4a,10,10a-hexahydro-1H-phenanthren-9-one (58.0 mg, 0.17 mmol), sodium borohydride (52.0 mg, 1.40 mmol), ethanol (3.0 mL), tetrahydrofuran (3.0 mL), stir, and reflux under a nitrogen atmosphere. After 2 hours, cool to ambient temperature, and concentrate in vacuo. Add ethyl acetate to reaction mixture, wash with sat ammonium chloride solution(aq), Brine, and dry over sodium sulfate. Concentrate to yield the titled compound (57.0 mg, 99%) as a white solid. TLC Rf=0.12 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.50 (d, 1H, J=8.8 Hz), 7.20 (d, 2H, J=8.4 Hz), 6.93 (d, 2H, J=8.4 Hz), 6.80 (dd, 1H, J=8.6, 2.4 Hz), 6.66 (m, 1H), 4.77 (d, 1H, J=9.7 Hz), 3.82 (m, 6H), 3.05 (m, 1H), 2.85 (m, 1H), 2.35 (m, 1H), 1.75 (m, 4H), 1.40 (m, 5H).

Provenance & Evidence