3-Hydroxypyridine → 3-(Oxiran-2-ylmethoxy)pyridine

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Reaction Steps

Sodium hydride (60%, 2.16 g, 54.0 mmol) was added portionwise into N,N-dimethylformamide (50 mL) with stirring at room temperature under a nitrogen atmosphere. A solution of 3-pyridinol (4.5 g, 46.28 mmol) in N,N-dimethylformamide (50 mL) was then added dropwise to this suspension over a period of 0.5 hour. After stirring for 1 hour a solution of (2S)-oxiranylmethyl 3-nitrobenzenesulfonate (10 g, 38.57 mmol) in N,N-dimethylformamide (50 mL) was added dropwise into this mixture over a period of 15 minutes. The mixture was then stirred at room temperature overnight. The reaction was quenched with aqueous ammonium chloride to pH 5 and extracted with ethyl acetate. The extracts were washed with water and dried with brine. Evaporation and purification by flash column chromatography (dichloromethane/methyl alcohol 95/5) gave a brown oil (1.44 g, 25% yield); 1H NMR (400 MHz, DMSO-d6) δ 2.71-2.73 (m, 1H), 2.81-2.84 (m, 1H), 3.34-3.38 (m, 1H), 3.87-3.92 (m, 1H), 4.40-4.43 (m, 1H), 7.30-7.33 (m, 1H), 7.39-7.41 (m, 1H), 8.17-8.19 (m, 1H), 8.31 (s, 1H); MS (ES) m/z: 152 (MH+).

Provenance & Evidence