Imidazole → methyl 2-(benzyloxy)-4-(1H-imidazol-1-yl)benzoate

Participants

Reaction Conditions

Reaction Steps

1H-Imidazole (0.044 g), D-proline (0.013 g), potassium carbonate (0.15 g), and copper(I) iodide (0.010 g) were added to a dimethyl sulfoxide (1 mL) solution of methyl 2-(benzyloxy)-4-iodobenzoate (0.20 g), followed by stirring under a nitrogen atmosphere at 90° C. for 1 hour. The reaction mixture was cooled to room temperature, and then dimethyl sulfoxide (0.5 mL), D-proline (0.013 g), and copper(I) iodide (0.010 g) were added thereto, followed by stirring under a nitrogen atmosphere at 90° C. for 2 hours. After cooling the reaction mixture to room temperature, water and ethyl acetate were added thereto, and the insoluble substance was removed by filtration. The organic layer was separated, washed with water and a saturated aqueous solution of sodium chloride sequentially, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography [Fuji Silysia Chemical Ltd., PSQ100B (spherical), eluent: 90-20% hexane/ethyl acetate] to obtain 0.13 g of methyl 2-(benzyloxy)-4-(1H-imidazol-1-yl)benzoate as a white solid.

Provenance & Evidence