Reacción #1788

ord-bfc9e545236f4da9864ea3f99c2d6fe8

Ecuación de reacción

Cc1ccnc(C)c1CO
2,4-dimethyl-3-hydroxymethylpyridine
O=S(Cl)Cl
thionyl chloride
Cc1ccnc(C)c1CCl
2,4-dimethyl-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 and saturated aqueous sodium bicarbonate
  3. 3
    SecadoThe organic layer was dried with MgSO4
  4. 4
    Filtraciónfiltered
  5. 5
    Otrothe solvent removed under reduced pressure

Procedimiento

The 2,4-dimethyl-3-hydroxymethylpyridine (19.2 g, 140 mmol) was dissolved in CH2Cl2 (800 mL) and cooled under nitrogen to 0° C. and thionyl chloride (125 mL) was slowly added and the reaction was stirred for 18 hours. The solvent was removed under reduced pressure and the residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate. The organic layer was dried with MgSO4, filtered and the solvent removed under reduced pressure to give the desired 2,4-dimethyl-3-chloromethylpyridine.

Fuente

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