Hydrochloric Acid → 3-(2-Methyl-4-{1-[4-methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethoxymethyl}-phenyl)-propionic Acid

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Reaction Steps

A mixture of 1-[4-Methyl-2-(4-trifluoromethyl-phenyl)-oxazol-5-yl]-ethanol (0.132 g, 0.487 mmol), sodium hydride (0.05 g, 1.25 mmol) and N,N-dimethyl formamide (5 mL) is stirred at room temperature. 3-(4-Iodomethyl-2-methyl-phenyl)-propionic acid methyl ester (0.17 g, 0.535 mmol) is added and the mixture is heated to 65 deg C., 2 hr. The reaction is cooled to room temperature and diluted with aqueous sodium hydroxide (10 mL, 5M) and stirred 1 hr. The pH is adjusted with aqueous hydrochloric acid until pH is 2–3. The product is extracted into ethyl acetate (3×25 mL). The combined extracts are dried over anhydrous magnesium sulfate, filtered and concentrated. The residue is purified via silica chromatography eluting with 7:3 hexanes:ethyl acetate to 1:1 hexanes:ethyl acetate to afford the title compound as a white solid, 0.027 g, 12%. MS M++1 448. The structure is confirmed by 1H NMR spectroscopy.

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