Tetrahydrofuran → [6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol

Participants

Reaction Steps

Combine 6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester (4.25 g, 11.17 mmol), lithium aluminum hydride (1.20 g, 32.39 mmol), and tetrahydrofuran (150 mL), and reflux under nitrogen atmosphere. After 3 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 5% to 30% ethyl acetate/hexanes to yield the titled compound (3.54 g, 90%) as a white solid. TLC Rf=0.13 in 4:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.43 (d, 1H, J=8.8 Hz), 7.26 (d, 2H, J=8.4 Hz), 7.00 (m, 1H), 6.93 (d, 2H, J=8.8 Hz), 6.84 (dd, 1H, J=8.4, 2.6 Hz), 4.05 (dd, 1H, J=11.2, 3.3 Hz), 3.86 (m, 6H), 3.62 (dd, 1H, J=11.0, 2.6 Hz), 3.34 (m, 3H), 2.49 (d, 1H, J=13.7 Hz), 1.95 (m, 1H), 1.65 (m, 2H), 1.45 (m, 2H), 1.30 (m, 1H), 1.16 (m, 2H).

Provenance & Evidence