Methyl iodide → 4-(5-Methoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one

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Reaction Steps

To a solution of 4-(5-hydroxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one (0.125 g, 0.495 mmol) (Example 6d) in DMF (2 mL) is added sodium hydride (0.018 g, 0.495 mmol). The reaction mixture is stirred at room temperature for 5 min and then methyl iodide (0.028 mL, 0.495 mmol) is added. The reaction is stirred for 2.5 h at room temperature. It is then washed with water and extracted with ethyl acetate twice. The organic layer is dried over Na2SO4 and concentrated in vacuo. The residue is purified by silica gel chromatography (dichloromethane-methanol, 19:1) to give 4-(5-methoxymethyl-imidazol-1-yl)-3,3-dimethyl-isochroman-1-one; MS (ESI) m/z 287.2 (M+H); 1H NMR (400 MHz, MeOD) δ ppm 1.70 (s, 3H), 1.77 (s, 3 H), 3.90 (s, 3 H), 4.39 (s, 2 H), 4.88 (br. s, 1 H), 6.99 (s, 1 H), 7.44-7.53 (m, 1H), 7.56-7.64 (m, 2 H), 7.76 (s, 1 H), 7.86 (d, J=7.6 Hz, 1 H).

Provenance & Evidence