Triethylamine → 2-(5-Methyl-2-phenyl-1,3-oxazol-4-yl)ethyl methanesulfonate

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Reaction Steps

2-(5-Methyl-2-phenyloxazol-4-yl)ethanol (20 g) and triethylamine (19.2 ml) were added to methylene chloride (200 ml) and, after dropwise addition of methanesulfonyl chloride (9.52 ml) at 0° C., the mixture was stirred at the same temperature for 15 min. The reaction mixture was washed with 10% aqueous citric acid solution (200 ml), saturated aqueous sodium hydrogen carbonate (100 ml) and saturated brine (100 ml), and dried (Na2SO4). Methylene chloride was evaporated under reduced pressure and the obtained residue was purified by column chromatography to give the title compound (21.45 g). 1H-NMR (CDCl3) δ (ppm); 2.53 (3H, s), 2.94 (3H, s), 2.94 (2H, t, J=7.0 Hz), 4.52 (2H, t, J=7.0 Hz), 7.30-7.50 (3H, m), 7.80-8.10 (2H, m).

Provenance & Evidence