Carbon Tetrachloride → 3-(Chloromethyl)-2-methoxy-6-methylpyridine

HRID 1837708Notes

Reaction equation

HRID 1837708 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10]O)=[CH:4][CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:32]>>[CH3:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[C:5]([CH2:10][Cl:32])=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 22678477HCID 22678477, compound

Product 1

HCID 226786093-(Chloromethyl)-2-methoxy-6-methylpyridine

Procedure

3.78 g of 6-methyl-2-methoxy-3-pyridinemethanol was dissolved in 60 ml of carbon tetrachloride, 6.48 g of triphenylphosphine was added thereto, and the mixture was heated under reflux for 6 hours 30 minutes. The solvent was evaporated, n-hexane was added to the residue, and the insoluble matters were filtered off. The filtrate was evaporated, and the crude product was purified by silica gel chromatography (n-hexane:ethyl acetate=100:1), to give 2.29 g of the title compound as a colorless oil.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 6 hours 30 minutes
  3. customThe solvent was evaporated
  4. additionn-hexane was added to the residue
  5. filtrationthe insoluble matters were filtered off
  6. customThe filtrate was evaporated
  7. customthe crude product was purified by silica gel chromatography (n-hexane:ethyl acetate=100:1)

Sources & evidence

ORD record
ord-8c4ddcd777914af59642bcff4f90425b
Source dataset
uspto-grants-2004_08
Patent number
US06784192B2

Reaction notes

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