Methanol → 6-Methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester

Participants

Reaction Steps

Combine methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-carboxylic acid methyl ester (9.95 g, 26.15 mmol), NaOMe (0.283 g, 5.23 mmol), methanol (32 mL), and tetrahydrofuran (125 mL), and stir under nitrogen atmosphere at 40° C. After 3 hours, concentrate reaction to dryness and add ethyl acetate. Wash with water and then brine, dry the organic phase with anhydrous sodium sulfate and concentrate to yield the titled compound (10.03 g, 99%) as a yellow-white solid. TLC Rf=0.25 in 6:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.27 (d, 2H, J=8.8 Hz), 7.20 (d, 1H, J=8.4 Hz), 6.99 (m, 1H), 6.90 (d, 2H, J=8.4 Hz), 6.77 (dd, 1H, J=8.4, 2.6 Hz), 4.36 (d, 1H, J=12.3 Hz), 3.84 (m, 6H), 3.60 (s, 3H), 3.54 (dd, 1H, J=12.6, 2.9 Hz), 3.36 (s, 1H), 2.51 (d, 1H, J=14.1 Hz), 2.01 (m, 1H), 1.72 (m, 2H), 1.45 (m, 2H), 1.11 (m, 3H).

Provenance & Evidence