Tetrahydrofuran → 6-Methoxy-10-(4-methoxy-phenyl)-9-methyl-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 (0.471 g, 0.93 mmol), lithium aluminum hydride (0.069 g, 1.86 mmol), and tetrahydrofuran (8.0 mL), and reflux under nitrogen atmosphere. After 5 hours, quench reaction by adding reaction to a stirred solution of Rochelle's salt (Na K Tartrate) and ethyl acetate. After several hours, separate the organic phase and wash with brine. Dry the organic phase with anhydrous sodium sulfate and flash chromatograph using 0% to 20% ethyl acetate/hexanes to yield the titled compound (0.267 g, 85%) as a white solid. TLC Rf=0.43 in 3:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.35 (d, 1H, J=8.4 Hz), 7.23 (d, 2H, J=8.4 Hz), 6.94 (m, 3H), 6.82 (dd, 1H, J=8.8, 2.6 Hz), 3.86 (s, 6H), 3.31 (m, 2H), 2.82 (dd, 1H, J=11.9, 2.6 Hz), 2.50 (d, 1H, J=13.7 Hz), 1.89 (m, 1H), 1.64 (m, 2H), 1.44 (m, 2H), 1.16 (m, 6H).

Provenance & Evidence