Hydrochloric Acid → HCID 66652226, compound

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Reaction Steps

Combine Na (0.013 g, 0.53 mmol) and methanol (2 ml) at 0-5° C. and stir until solution forms. Add 6-Bromomethyl-4-(4-hydroxy-phenyl)-2,3,3a,4,5,9b-hexahydro-1H-cyclopenta[a]naphthalen-8-ol (0.037 g, 0.1 mmol) and stir for 3 hours. Remove solvent in vacuo. Take into ethyl acetate and 1N HCl. Separate organic layer and wash with water. Dry over anhydrous sodium sulfate and remove solvent in vacuo. The residue is chromatographed on silica gel with 25% ethyl acetate/hexanes to yield the titled compound (0.012 g, 37%). 1H NMR (DMSO-d6): 9.16(s, 1H), 9.04 (s, 1H), 7.11 (d, J=7.9 Hz, 2H), 6.71 (d, J=8.8 Hz, 2H), 6.58 (s, 1H), 6.53 (s, 1H), 4.35 (dd, j=16 and 7 Hz, 2H), 3.4 (m, 1H presumed), 3.0 (m, 1H), 2.76 (m, 1H), 2.65 (m, 1H), 2.45(m, 1H) 2.15 (m, 1H), 1.6-1.2 (m, 5H). MS m/z 323 (M−1).

Provenance & Evidence