Reaction #66132

Reaction equation

2,6-dichloro-4-methyl-pyridine

sodium methoxide

→

2-chloro-6-methoxy-4-methyl-pyridine

Yield 63.5%

Solvents

methanol

Conditions

Workup

1. 1
   Temperatureheated
2. 2
   Temperatureat reflux for 48 h
3. 3
   OtherThe solvent was evaporated
4. 4
   Otherthe residue partitioned between water and dichloromethane
5. 5
   OtherThe organic layer was separated
6. 6
   Washwashed with water, brine
7. 7
   Dryingdried over anhydrous sodium sulfate
8. 8
   Concentrationconcentrated

Procedure

A solution of 2,6-dichloro-4-methyl-pyridine (250 mg, 1.5 mmol) in methanol (2 mL) was added to a solution of sodium methoxide (prepared from sodium (71 mg, 3.0 mmol) and anhydrous methanol (20 mL)) and heated at reflux for 48 h. The solvent was evaporated and the residue partitioned between water and dichloromethane. The organic layer was separated, washed with water, brine, dried over anhydrous sodium sulfate and concentrated to afford 2-chloro-6-methoxy-4-methyl-pyridine (150 mg, 61%) as a pale orange oily liquid.

Source