Reaktion #1788

ord-bfc9e545236f4da9864ea3f99c2d6fe8

Reaktionsgleichung

Cc1ccnc(C)c1CO
2,4-dimethyl-3-hydroxymethylpyridine
O=S(Cl)Cl
thionyl chloride
Cc1ccnc(C)c1CCl
2,4-dimethyl-3-chloromethylpyridine

Lösungsmittel

Reaktionsbedingungen

Temperatur
0°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe solvent was removed under reduced pressure
  2. 2
    Sonstigethe residue was partitioned between CH2Cl2 and saturated aqueous sodium bicarbonate
  3. 3
    TrocknenThe organic layer was dried with MgSO4
  4. 4
    Filtrationfiltered
  5. 5
    Sonstigethe solvent removed under reduced pressure

Vorschrift

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.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05726172uspto-grants-1998_03