Water → 2-chloro-3-(methoxymethoxy)Pyridine

Sodium hydride (66%, 633 mg, 17.4 mmol) was added to an ice-cooled solution of 2-chloro-3-hydroxypyridine (2.05 g, 15.8 mmol) in tetrahydrofuran (30 ml) under nitrogen atmosphere, and this reaction mixture was stirred at that temperature for 15 minutes. Chloromethyl methyl ether (1.32 ml, 17.4 mmol) was added, and the resulting reaction mixture was stirred at that temperature for 30 minutes, then at room temperature for another 2 hours. After water was added, the reaction mixture was extracted with ethyl acetate, washed with saturated brine, and then concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give the title compound (2.44 g).

1. customthe resulting reaction mixture
2. stirringwas stirred at that temperature for 30 minutes
3. waitat room temperature for another 2 hours
4. extractionthe reaction mixture was extracted with ethyl acetate
5. washwashed with saturated brine
6. concentrationconcentrated under reduced pressure
7. customThe residue was purified by silica gel column chromatography

ORD record

ord-5a60bc25dfb941929fb189a534cc6cb1

Source dataset

uspto-grants-2011_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07999090B2