Reaction #1782

Reaction equation

2-ethyl-3-hydroxymethylpyridine

thionyl chloride

→

2-ethyl-3-chloromethylpyridine

Solvents

CH2Cl2

Conditions

Workup

1. 1
   OtherThe solvent was removed under reduced pressure
2. 2
   Otherthe residue was partitioned between CH2Cl2 (100 mL) and saturated aqueous sodium bicarbonate (100 mL)
3. 3
   DryingThe organic layer was dried with MgSO4
4. 4
   Filtrationfiltered
5. 5
   Otherthe solvent removed under reduced pressure

Procedure

The 2-ethyl-3-hydroxymethylpyridine (2.3 g, 16.8 mmol) was dissolved in CH2Cl2 (100 mL) and cooled under nitrogen to 0° C. and thionyl chloride (7.0 mL) was slowly added and the reaction was stirred for 3 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 (100 mL) and saturated aqueous sodium bicarbonate (100 mL). The organic layer was dried with MgSO4, filtered, and the solvent removed under reduced pressure to give the desired 2-ethyl-3-chloromethylpyridine.

Source