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

Participants

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, 1 H), 2.81–2.84 (m, 1 H), 3.34–3.38 (m, 1 H), 3.87–3.92 (m, 1 H), 4.40–4.43 (m, 1 H), 7.30–7.33 (m, 1 H), 7.39–7.41 (m, 1 H), 8.71–8.19 (m, 1 H), 8.31 (s, 1 H); MS (ES) m/z: 152 (MH+).

Provenance & Evidence