Trichloroacetyl chloride → 2-(Chloromethyl)-3,4-dimethylpyridine

HRID 35462

Reaktionsgleichung

Reaktionsgleichung von HRID 35462
[CH3:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N+:3]=1[O-].[Cl:11]C(Cl)(Cl)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:11][CH2:1][C:2]1[C:7]([CH3:8])=[C:6]([CH3:9])[CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 187352862,3,4-Trimethyl-1-oxidopyridin-1-ium

Produkt 1

HCID 199965002-(Chloromethyl)-3,4-dimethylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  1. temperatureat reflux under argon
  2. additionis added
  3. extractionthe mixture is extracted with methylene chloride
  4. dry with materialthe methylene chloride solution is dried
  5. concentrationconcentrated
  6. customThe thus-obtained crude product
  7. customis chromatographed on silica gel (solvent: methylene chloride/ether [5:1])

Quellen und Nachweise

ORD-Eintrag
ord-b6036994e5e34e789174b720aa134be6
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766133

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