Trichloroacetyl chloride → 2-Chloromethyl-4-tert-butyl-3-methylpyridine

HRID 35459Notes

Reaction equation

HRID 35459 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][N+:8]([O-])=[C:7]([CH3:12])[C:6]=1[CH3:13])([CH3:4])([CH3:3])[CH3:2].[Cl:14]C(Cl)(Cl)C(Cl)=O.C(=O)(O)[O-].[Na+]>C(Cl)(Cl)Cl>[Cl:14][CH2:12][C:7]1[C:6]([CH3:13])=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 6420Trichloroacetyl chlorideHCID 516892Sodium BicarbonateHCID 536584744-tert-butyl-2,3-dimethylpyridine N-oxide

Product 1

HCID 212959572-Chloromethyl-4-tert-butyl-3-methylpyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 9.8 g of 4-tert-butyl-2,3-dimethylpyridine N-oxide in 120 ml of abs. chloroform is boiled at reflux under argon and treated through the condenser with 25.5 ml of trichloroacetyl chloride. After 22 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 [10:1]). The 2-chloromethyl-4-tert-butyl-3-methylpyridine obtained is processed directly.

Workup

  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 [10:1])

Sources & evidence

ORD record
ord-e812e4ec5734406e872ef7293d6f9d85
Source dataset
uspto-grants-1988_08
Patent number
US04766133

Reaction notes

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