4-(5-But-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one → 4-(5-Butyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Participants

Reaction Steps

To a solution of 4-(5-but-1-enyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.110 g, 0.37 mmol) in methanol (2 mL) is added Pd/C (0.020 g). The reaction vessel is flushed with hydrogen gas and stirred under balloon pressure overnight. The mixture is filtered and the filtrate concentrated in vacuo to give a residue which is purified by semi-preparative reverse phase HPLC to give 4-(5-butyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 299.1 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.02 (br. s, 3 H), 1.22 (s, 3 H), 1.53 (br. s, 5 H), 1.77 (br. s, 2 H), 2.81 (br. s, 2 H), 5.54 (br. s, 1 H), 6.82 (s, 1H), 7.19 (br. s, 1 H), 7.39 (d, J=7.3 Hz, 1 H), 7.60-7.67 (m, 1 H), 7.71-7.78 (m, 1 H), 8.21 (d, J=7.8 Hz, 1 H).

Provenance & Evidence