Methyl iodide → 6-Methoxy-9-methoxymethyl-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

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Reaction Steps

Combine [6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthren-9-yl]-methanol (0.084 g, 0.24 mmol), NaH (0.014 mg, 0.29 mmol), and DMF (3.0 mL) and stir under nitrogen atmosphere at −10° C. After 1 hour, add MeI (50 uL, 0.072 mmol) and stir at room temperature for 18 hours. Concentrate reaction under vacuum then add ethyl acetate and water, separated the organic phase and wash 2× with brine. Dry the organic phase over anhydrous sodium sulfate. Concentrate the organic phase under vacuum and flash chromatograph using 0% to 25% ethyl acetate/hexanes to yield the titled compound (0.057 g, 65%) as a white solid. TLC Rf=0.40 in 3:1 hexanes:ethyl acetate. 1H NMR (CDCl3): 7.58 (d, 1H, J=8.8 Hz), 7.25 (d, 2H, J=8.8 Hz), 6.93 (m, 3H), 6.81 (dd, 1H, J=8.4, 2.6 Hz), 3.85 (m, 6H), 3.66 (m, 1H), 3.38 (m, 2H), 3.23 (m, 4H), 3.11 (dd, 1H, J=11.9, 3.1 Hz), 2.48 (d, 1H, J=13.7 Hz), 1.92 (m, 1H), 1.42 (m, 2H), 1.18 (m, 3H), 1.77 (m, 2H).

Provenance & Evidence