Imidazole → Methyl 2-{[tert-butyl(dimethyl)silyl]oxy}-4-{[4-(methoxymethoxy)phenyl]ethynyl}benzoate

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To a solution of methyl 2-hydroxy-4-iodobenzoate (6.55 g, 23.6 mmol), 1-ethynyl-4-(methoxymethoxy)benzene (4.58 g, 28.3 mmol) and copper(I) iodide (450 mg, 2.36 mmol) in triethylamine (50 mL) was added bis(triphenylphosphine)palladium(II) chloride (1.66 mg, 2.36 mmol), and the mixture was stirred under an argon stream at room temperature for 30 min. The reaction mixture was diluted with ethyl acetate, and the mixture was washed with water, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was dissolved in DMF (30 mL). Imidazole (2.42 g, 35.4 mmol) and tert-butyl(chloro)dimethylsilane (4.27 g, 28.3 mmol) were added thereto, and the mixture was stirred at room temperature for 1.5 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed twice with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane:ethyl acetate=19:1 to 3:2) to give the title compound (8.50 g, yield 84%) as an oil.

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