Réaction #63740

Équation de réaction

2,3,4-trimethylpyridine N-oxide

trichloroacetyl chloride

sodium bicarbonate

→

2-chloromethyl-3,4-dimethylpyridine

Solvants

chloroform

Conditions de réaction

Traitement

1. 1
   Températureat reflux under argon
2. 2
   workup.ADDITIONis added
3. 3
   Extractionthe mixture is extracted with methylene chloride
4. 4
   Séchagethe methylene chloride solution is dried
5. 5
   Concentrationconcentrated
6. 6
   AutreThe thus-obtained crude product
7. 7
   Autreis chromatographed on silica gel (solvent: methylene chloride/ether [5:1])

Mode opératoire

A solution of 13.3 g of 2,3,4-trimethylpyridine N-oxide in 130 ml of abs. chloroform is boiled at reflux under argon and treated through the condenser with 33.2 ml of trichloroacetyl chloride. After 18 hours the reaction mixture is poured on to ice, whereupon 10% sodium bicarbonate solution is added, the mixture is extracted with methylene chloride and the methylene chloride solution is dried and concentrated. The thus-obtained crude product is chromatographed on silica gel (solvent: methylene chloride/ether [5:1]). The 2-chloromethyl-3,4-dimethylpyridine obtained is processed directly.

Source