Chloromethyl Methyl Ether → 3-Methoxymethoxy-5-phenylisoxazole

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Reaction Steps

3-Hydroxy-5-phenylisoxazole (8.05 g) was dissolved in dimethylformamide (80 ml), and sodium methoxide (28% methanol solution, 3.24 g) was added dropwise thereto, followed by stirring of the resulting mixture at room temperature for one hour. While the reaction mixture was cooled to 5° C., chloromethyl methyl ether (4.83 g) was added thereto, followed by stirring of the resulting mixture at the same temperature for one hour. The reaction mixture was poured into ice-cold water (200 ml) and extracted with ether (200 ml×2), and the organic layer was dried over anhydrous magnesium sulfate. After filtration, the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: hexane/ethyl acetate=4/1) to obtain the title compound (6.30 g, 61%) as a colorless oil.

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