Trichloroacetyl chloride → 2-(Chloromethyl)-3-methylpyridine

HRID 35447

Reaktionsgleichung

Reaktionsgleichung von HRID 35447
[CH3:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N+:3]=1[O-].[Cl:10]C(Cl)(Cl)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:10][CH2:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[CH:4][N:3]=1

Komponenten

5

Edukt 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 3840573Pyridine, 2,3-dimethyl-, 1-oxide

Produkt 1

HCID 130586822-(Chloromethyl)-3-methylpyridine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel

Versuchsvorschrift

A solution of 15 g (0.12 mol) of 2,3-dimethylpyridine 1-oxide in 75 ml of chloroform is boiled at reflux and treated as rapidly as possible with 37 ml of trichloroacetyl chloride (it is advantageous to add the acid chloride through the reflux condenser). The reaction mixture is heated under reflux for 2.5 hours, subsequently poured into a mixture of ice and sodium bicarbonate and the resulting solution is washed several times with methylene chloride. The organic phase is dried with sodium sulphate, filtered and concentrated. The residue is chromatographed on silica gel with methylene chloride, the medium pressure flash chromatography method being used and the pressure being produced with nitrogen gas. The 2-chloromethyl-3-methylpyridine obtained is processed directly.

Aufarbeitung

  1. temperatureat reflux
  2. temperatureThe reaction mixture is heated
  3. temperatureunder reflux for 2.5 hours
  4. washthe resulting solution is washed several times with methylene chloride
  5. dry with materialThe organic phase is dried with sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue is chromatographed on silica gel with methylene chloride
  9. customthe pressure being produced with nitrogen gas

Quellen und Nachweise

ORD-Eintrag
ord-7f7b70aae07c487b8c8cb35b623dcc2d
Quelldatensatz
uspto-grants-1988_08
Patentnummer
US04766133

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