Reaktion #1789

Reaktionsgleichung

2,4-dimethyl-3-chloromethylpyridine

m-chloroperbenzoic acid

→

2,4-dimethyl-3-chloromethylpyridine-N-oxide

Lösungsmittel

CHCl3

Reaktionsbedingungen

Aufarbeitung

1. 1
   ExtraktionThe solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL)
2. 2
   TrocknenThe organic phase was dried with MgSO4
3. 3
   Filtrationfiltered
4. 4
   Sonstigethe solvent removed under reduced pressure
5. 5
   SonstigeThe residue was chromatographed on silica gel
6. 6
   WaschenMeOH and eluted with same
7. 7
   Sonstigethe solvent was removed under reduced pressure the

Vorschrift

The 2,4-dimethyl-3-chloromethylpyridine (21.5 g, 138 mmol) was dissolved in CHCl3 (800 mL) and cooled under nitrogen to 0° C. and m-chloroperbenzoic acid (55%, 35 g) was added in small portions. The reaction was stirred for 4 hours. The solution was extracted twice with saturated aqueous sodium bicarbonate (500 mL). The organic phase was dried with MgSO4, filtered and the solvent removed under reduced pressure. The residue was chromatographed on silica gel packed in 98:2 CH2 Cl2 :MeOH and eluted with same. The appropriate fractions were combined and the solvent was removed under reduced pressure the give the desired 2,4-dimethyl-3-chloromethylpyridine-N-oxide.

Quelle