Ethanol → 2-Chloro-5-(ethoxymethyl)pyridine

2-Chloro-5-chloromethyl-pyridine (1 g, 6.2 mmol) was dissolved in 15 ml dry ethanol. After cooling in an ice bath NaH (248 mg 60%, 6.2 mmol) was added to this solution. The reaction was warmed to rt and stirred for 16 hours. After this time the reaction was quenched with 15 ml ice-water and extracted with ethyl acetate (2×50 ml). The combined organic layers were washed with brine, dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography using 5%-10% ethyl acetate in hexane to afford 400 mg of 2-Chloro-5-ethoxymethyl-pyridine (yield 37%).

1. additionwas added to this solution
2. customAfter this time the reaction was quenched with 15 ml ice-water
3. extractionextracted with ethyl acetate (2×50 ml)
4. washThe combined organic layers were washed with brine
5. dry with materialdried over sodium sulfate
6. concentrationconcentrated in vacuo
7. customThe residue was purified by column chromatography

ORD record

ord-69d7d3834c6c4c96b44bbbd20ca946d0

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299077B2