反应详情

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).

1. customquench
2. customreaction
3. additionby adding
4. waitAfter several hours
5. customseparate the organic phase
6. washwash with brine
7. dry with materialDry the organic phase with anhydrous sodium sulfate and flash chromatograph