Tetrahydrofuran → 9-Ethyl-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

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Reaction Steps

Combine toluene-4-sulfonic acid 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-ylmethyl ester (0.151 g, 0.30 mmol), methyl magnesium bromide (0.46 mL, 1.40 mmol), Li2CuCl4 (150 uL), and tetrahydrofuran (3 mL), and stir under nitrogen atmosphere. After 18 hours, concentrate reaction under vacuum and flash chromatograph using 0% to 10% ethyl acetate/hexanes to yield the titled compound (0.085 g, 81%) as a white foam. TLC Rf=0.60 in 8:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.32 (s, 1H), 7.24 (d, 2H, J=8.4 Hz), 6.94 (m, 3H), 6.81 (dd, 1H, J=8.4, 2.6 Hz), 3.86 (m, 6H), 3.42 (m, 1H), 3.23 (s, 1H), 3.08 (dd, 1H, J=12.1, 3.3 Hz), 2.49 (d, 1H, J=13.7 Hz), 1.93 (m, 2H), 1.67 (m, 1H), 1.57 (m, 2H), 1.44 (d, 2H, J=8.8 Hz), 1.19 (m, 3H), 0.62 (t, 3H, J=7.3 Hz).

Provenance & Evidence