Tetrahydrofuran → 6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-1,2,3,4,4a,10a-hexahydro-phenanthrene

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Reaction Steps

Combine trifluoro-methanesulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,10a-hexahydro-phenanthren-9-yl ester (0.523 g, 1.12 mmol), Pd-tetrakis (45.0 mg, 0.04 mmol), and tetrahydrofuran (10.0 mL), and stir under nitrogen atmosphere at 0° C. After 15 minutes, add dimethylzinc (3.5 mL, 3.44 mmol) dropwise. Allow the reaction to warm to room temperature and stir for 18 hours, then heat reaction at 40° C. for 3 hours. Add ethyl acetate and water. Wash the organic phase with brine, dry over anhydrous sodium sulfate, concentrate, and chromatograph eluting with 0% to 20% ethyl acetate/hexanes to yield the titled compound (0.224 g, 60%) as a white solid. TLC Rf=0.30 in 5:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.32 (s, 1H), 7.20 (d, 2H, J=8.8 Hz), 6.95 (m, 3H), 6.79 (m, 1H), 3.88 (m, 6H), 3.21 (m, 1H), 2.46 (m, 2H), 1.97 (s, 3H), 1.74 (m, 1H), 1.55 (m, 3H), 1.38 (m, 1H), 1.15 (m, 2H).

Provenance & Evidence