Reaction #684967

Reaction equation

Chloromethyl methyl ether

2-chloro-3-hydroxypyridine

Sodium hydride

water

→

title compound

Yield 89.0%

2-Chloro-3-(methoxymethoxy)pyridine

Yield 89.0%

Solvents

tetrahydrofuran

Conditions

Workup

1. 1
   Otherthe resulting reaction mixture
2. 2
   workup.STIRRINGwas stirred at that temperature for 30 minutes
3. 3
   workup.WAITat room temperature for another 2 hours
4. 4
   Extractionthe reaction mixture was extracted with ethyl acetate
5. 5
   Washwashed with saturated brine
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   OtherThe residue was purified by silica gel column chromatography

Procedure

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).

Source