4-[5-(1-Hydroxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one → 4-(5-Acetyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-[5-(1-hydroxy-ethyl)-imidazol-1-yl]-3,3-dimethyl-isochroman-1-one (0.100 g, 0.35 mmol) (Example 12) in dioxane (2 mL) is added manganese dioxide (0.46 g, 5.2 mmol) and the reaction mixture is heated to 60° C. overnight. Filtration through celite and concentration in vacuo gave a residue, which is purified by semi-preparative reverse phase HPLC to give 4-(5-acetyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one as a white solid; MS (ESI) m/z 285.0 (M+H); 1H NMR (400 MHz, CDCl3) δ ppm 1.22 (s, 3 H), 1.55 (s, 3 H), 2.61 (s, 3 H), 6.90 (s, 1 H), 7.38 (d, J=7.1 Hz, 1 H), 7.47 (s, 1 H), 7.57-7.62 (m, 1 H), 7.63-7.69 (m, 1 H), 7.93 (s, 1 H), 8.28 (dd, J=7.6, 1.5 Hz, 1 H).

Provenance & Evidence