Chloromethyl Methyl Ether → 2-Fluoro-5-(1-methoxymethoxy-ethyl)-pyridine

Participants

Reaction Conditions

Reaction Steps

Add N,N′-diisopropylethylamine and chloromethoxymethane to a solution of 1-(6-fluoro-pyridin-3-yl)-ethanol (3.0 g, 21.3 mmol) in dichloromethane at 0° C. Continue to stir the mixture for 30 min at 0° C., then overnight at room temperature. Dilute the mixture with chloroform/isopropyl alcohol (3/1). Wash the solution with saturated aqueous sodium chloride. Dry it over sodium sulfate. Concentrate the solution in vacuo to a dark residue. Purify by column chromatography (hexane→20% ethyl acetate in hexane) to afford the product as a colorless solid (3 g, 66%). MS (ES) m/z 186 [M+1]+.

Provenance & Evidence