Reacción #1782

ord-090d23f63738479ca8c99ffd51c34f39

Ecuación de reacción

CCc1ncccc1CO
2-ethyl-3-hydroxymethylpyridine
O=S(Cl)Cl
thionyl chloride
CCc1ncccc1CCl
2-ethyl-3-chloromethylpyridine

Disolventes

Condiciones de reacción

Temperatura
0°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe solvent was removed under reduced pressure
  2. 2
    Otrothe residue was partitioned between CH2Cl2 (100 mL) and saturated aqueous sodium bicarbonate (100 mL)
  3. 3
    SecadoThe organic layer was dried with MgSO4
  4. 4
    Filtraciónfiltered
  5. 5
    Otrothe solvent removed under reduced pressure

Procedimiento

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.

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US05726172uspto-grants-1998_03