Potassium Cyanide → HCID 66652174, 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), KCN (0.010 g, 0.15 mmol), and 18-crown-6 (0.043 g, 0.16 mmol) and heat at 80° C. for 2 hours. Cool, add ice and extract with ethyl acetate. Wash organic layer with sodium bicarbonate solution sat., then 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 (0.022 g, 70%). 1H NMR (DMSO-d6) 9.27(s, 1H), 9.18 (s, 1H), 7.13 (d, J=8.4 Hz, 2H), 6.73 (d, J=7.9 Hz, 2H), 6.66 (s, 1H), 6.59 (s, 1H), 3.95 (s, 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 318 (M−1).

Provenance & Evidence