Chloromethyl Methyl Ether → 1-Methoxymethyl-1H-imidazole-4-carboxylic acid methylester

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Reaction Steps

Imidazole-4-carboxylic acid methylester (5.00 g) was dissolved in acetonitrile (100 mL), and under ice cooling and stirring, were added TEA (11.1 mL) and then chloromethylmethylether (4.47 mL), followed by heating to reflux for 3 days. After being allowed to cool to room temperature, the mixture was diluted with ethyl acetate, and washed with saturated brine. The organic layer was dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (methanol/chloroform=0%→7%) using silica gel column (product name: Hi-Flash Column 5 L, manufactured by Yamazen Corporation) to afford the title compound (3.64 g).

Provenance & Evidence