4-[5-(2-Methoxy-vinyl)-imidazole-1-yl]-3,3-dimethyl-isochroman-1-one → 4-[5-(2-Methoxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one

Participants

Reaction Steps

To a solution of 4-[5-(2-methoxy-vinyl)-imidazole-1-yl]-3,3-dimethyl-isochroman-1-one (0.110 g, 0.37 mmol) in methanol (5 mL) is added Pd/C (0.020 g). The reaction vessel is flushed with hydrogen gas and stirred under balloon pressure for 72 h. The mixture is filtered, and the filtrate concentrated in vacuo to give a residue which is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 4-[5-(2-methoxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one as a white solid; HRMS (ESI) m/z 301.1555 [(M+H)+: Calcd for C17H20N2O3: 301.1552]; 1H NMR (400 MHz, MeOD) δ ppm 1.25 (s, 3 H), 1.56 (s, 3H), 3.13 (br. s, 2 H), 3.45 (br. s, 3 H), 3.70-3.79 (m, 2 H), 5.71 (s, 1 H), 6.90 (s, 1 H), 7.15 (br. s, 1 H), 7.52 (d, J=7.6 Hz, 1 H), 7.60-7.72 (m, 1 H), 7.74-7.86 (m, 1 H), 8.24 (dd, J=7.8, 1.5 Hz, 1 H)

Provenance & Evidence