반응 #648183

반응 방정식

6-fluoro-pyridin-3-ol

sodium hydride

chloromethyl methyl ether

→

title compound

수율 109.5%

2-Fluoro-5-methoxymethoxy-pyridine

수율 109.5%

용매

ethyl acetate

water

dimethylformamide

반응 조건

후처리

1. 1
   workup.STIRRINGStir the mixture at room temperature overnight
2. 2
   세척Wash the organic layer with water and saturated aqueous sodium chloride
3. 3
   건조Dry the mixture over sodium sulfate
4. 4
   농축Concentrate the solution in vacuo to brown oil
5. 5
   기타Purify by column chromatography (10% ethyl acetate in hexane)

실험 절차

Add 6-fluoro-pyridin-3-ol (3.5 g, 30.95 mmol) to a suspension of sodium hydride (1.49 g, 37.14 mmol) in dimethylformamide (20 mL). Stir the mixture for 1 hour. Add chloromethyl methyl ether (2 g, 25.0 mmol). Stir the mixture at room temperature overnight. Dilute the mixture with ethyl acetate and water. Wash the organic layer with water and saturated aqueous sodium chloride. Dry the mixture over sodium sulfate. Concentrate the solution in vacuo to brown oil. Purify by column chromatography (10% ethyl acetate in hexane) to afford the title compound (4.30 g, 88.4%) as yellow oil. 1H NMR (400 MHz, CDCl3) δ 3.48 (s, 3H), 5.15 (s, 2H), 6.85 (dd, J=3.6 Hz, J=8.8 Hz, 1H), 7.47 (m, 1H), 7.96 (m, 1H).

출처