Chloromethyl Methyl Ether → HCID 11701122, compound

Under argon atmosphere, into a solution of 5-chloro-3-pyridinol (5.0 g, 38.6 mmol) in 100 mL of dry tetrahydrofuran at room temperature was added 60% sodium hydride (1.85 g, 46.3 mmol). After stirring the mixture for 1 hour at room temperature, a solution of chloromethyl methyl ether (3.42 g, 42.6 mmol) in 10 mL of dry tetrahydrofuran was added over 10 min. The resulting mixture was heated to reflux for 16 hours. The solvent was evaporated, and the residue was diluted with ethyl acetate, then washed with 1N aq. NaOH. The combined organic layer was then concentrated to give the crude material. Column chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v/), gave the desired product (6.52 g, 97%).

1. temperatureThe resulting mixture was heated
2. temperatureto reflux for 16 hours
3. customThe solvent was evaporated
4. additionthe residue was diluted with ethyl acetate
5. washwashed with 1N aq. NaOH
6. concentrationThe combined organic layer was then concentrated
7. customto give the crude material
8. washColumn chromatography on silica gel, eluting with ethyl acetate/hexane (30/70, v/v/)

ORD record

ord-fbeb8bf9de45447f8a52c74d8e844571

Source dataset

uspto-grants-2003_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06653310B2