Dimethyl Sulfoxide → HCID 72309404, compound

Participants

Reaction Steps

Combine 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), trimethylamine N-oxide (0.03 g, 0.4 mmol), DMSO (1.5 ml), and methylene chloride (0.5 ml) and stir at 0-5° C. for 30 minutes. Add water and ethyl acetate. Wash organic layer 5× with water, dry over anhydrous sodium sulfate and concentrate to a residue which yields after separation on silica gel with 33% EtOAC/hexanes, the titled compound (0.12 g, 39%). 1H NMR (CD3OD) 10.26 (s, 1H), 7.18 (d, J=8.4, Hz, 2H), 7.12 (s, 1H), 6.97 (s, 1H), 6.77 (d, J=7.9 Hz, 2H), 3.4 (m, 1H), 3.15 (m, 1H), 3.0 (m, 2H), 2.55(m, 1H) 2.2 (m, 1H), 1.6-1.2. MS m/z 307 (M−1).

Provenance & Evidence