反应详情

To a solution of 3-(benzyloxy)-4-bromo-5-methoxy-N-(prop-2-yn-1-yl)benzamide (0.455 g, 1.22 mmol) in dioxane (12 mL) was added sodium hydride (60% wt, 0.146 g, 3.65 mmol) and the mixture was heated at reflux for six hours. The mixture was cooled to room temperature, quenched by slow addition of water, and diluted with ethyl acetate. The mixture was washed with water, saturated sodium bicarbonate, brine, then dried over magnesium sulfate and concentrated. Flash column chromatography (12 g silica, 2% ethyl acetate in DCM) provided 2-(3-(benzyloxy)-4-bromo-5-methoxyphenyl)-5-methyloxazole (198 mg) as an off-white solid. MS=374 (M+1). 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 7.55 (d, J=7.58 Hz, 2H), 7.43 (t, J=7.33 Hz, 2H), 7.32-7.39 (m, 2H), 7.27 (d, J=2.02 Hz, 1H), 6.89 (d, J=1.01 Hz, 1H), 5.27 (s, 2H), 4.02 (s, 3H), 2.44 (d, J=1.52 Hz, 3H).

1. temperature0.146 g, 3.65 mmol) and the mixture was heated
2. temperatureat reflux for six hours
3. customquenched by slow addition of water
4. additiondiluted with ethyl acetate
5. washThe mixture was washed with water, saturated sodium bicarbonate, brine
6. dry with materialdried over magnesium sulfate
7. concentrationconcentrated