Reaction Steps
Combine [6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol (1.45 g, 3.81 mmol), TosCl (0.80 g, 4.19 mmol), Et3N (1.2 mL, 8.38 mmol), 2,6-dimethylaminopyridine (140.0 mg, 1.14 mmol), and methylene chloride (30 mL), and stir under nitrogen atmosphere at room temperature. After 18 hours, concentrate reaction under vacuum 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 (1.83 g, 95%) as a yellowish-white solid. TLC Rf=0.30 in 2:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.53 (d, 2H, J=8.4 Hz), 7.22 (d, 2H, J=8.4 Hz), 7.16 (d, 1H, J=8.8 Hz), 7.06 (d, 2H, J=8.8 Hz), 6.92 (d, 1H, J=2.2 Hz), 6.83 (d, 2H, J=8.4 Hz), 6.66 (dd, 1H, J=8.8, 2.6 Hz), 4.34 (dd, 1H, J=9.7, 2.6 Hz), 4.03 (dd, 1H, J=9.7, 4.0 Hz), 3.85 (s, 6H), 3.48 (d, 1H, J=11.9 Hz), 3.20 (s, 1H), 3.09 (dd, 1H, J=12.1, 3.3 Hz), 2.46 (s, 3H), 1.89 (m, 1H), 1.61 (m, 3H), 1.41 (d, 2H, J=9.7 Hz), 1.14 (m, 3H).
