Chloromethyl Methyl Ether → 5-(Methoxymethoxy)pyridine-2-carbonitrile

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Reaction Steps

60% sodium hydride (3.62 g, 90.4 mmol) was added to an N,N-dimethylformamide (70 mL) solution of 5-hydroxypyridin-2-carbonitrile (7.24 g, 60.3 mmol) at 0° C., and the mixture was stirred at the same temperature for 15 minutes. Subsequently, chloromethyl methyl ether (9.16 ml, 121 mmol) was added to the mixture little by little, and the resulting mixture was further stirred at the same temperature for 45 minutes. A saturated aqueous solution of ammonium chloride and water were added to the reaction mixture, and the mixture was extracted twice with ethyl acetate. The organic layer thus obtained was washed with brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resulting residue was purified by silica gel column chromatography (hexane:ethyl acetate=75:25, v/v) to give the title compound (8.63 g, yield: 87%).

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