Hydrochloric Acid → 6,7-Dimethoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene

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Reaction Steps

Combine 7-Bromo-6-methoxy-10-(4-methoxy-phenyl)-1,2,3,4,4a,9,10,10a-octahydro-phenanthrene (chiral) (0.025 g, 0.06 mmol), NaOMe 5N (1.4 ml, 7 mmol), CuIBr (0.005 g, 0.034 mmol) and ethyl acetate (0.005 ml, 0.05 mmol) and heat at 115° C. for 1.5 hours. Cool, and add 1N HCl and extract with ethyl acetate. Wash organic layer with water, dry over anhydrous sodium sulfate and remove solvent in vacuo. Chromatograph on silica gel with 9% ethyl acetate/hexanes to yield the titled compound (0.012 g, 55%). 1H NMR (CDCl3). MS m/z 352.9 (M+1).

Provenance & Evidence