Ethyl Acetate → 2-[3-(2-{[Tert-butyl(dimethyl)silyl]oxy}-ethoxy)-4-methylphenyl]-1,3-benzoxazole

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A solution of 5-(1,3-benzoxazol-2-yl)-2-methylphenol (355 mg, 1.6 mmol) in DMF (10 mL) was cooled to 0° C. and NaH (70 mg, 1.7 mmol) was added slowly. After 15 min, (2-bromoethoxy)(tert-butyl)dimethylsilane (370 μL, 1.7 mmol) was added. The reaction was then elevated to 90° C. for 1 h and EtOAc (100 mL) was added. The EtOAc solution was washed with brine (3×20 mL), dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash column (silica gel, hexanes:EtOAc 1:5) to afford 2-[3-(2-{[tert-butyl(dimethyl)silyl]oxy}-ethoxy)-4-methylphenyl]-1,3-benzoxazole.

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