Ethanol → 4-Ethoxy-3-methoxy-2-methylpyridine

HRID 649211Notes

Reaction equation

HRID 649211 reaction equation
Cl[C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10].[Na].[CH2:12]([OH:14])[CH3:13]>>[CH2:12]([O:14][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([CH3:8])[C:3]=1[O:9][CH3:10])[CH3:13]

Participants

4

Reactant 3

HCID 702EthanolHCID 5360545SodiumHCID 105830464-Chloro-3-methoxy-2-methylpyridine

Product 1

HCID 201427994-Ethoxy-3-methoxy-2-methylpyridine

Procedure

4-Chloro-3-methoxy-2-methylpyridine (3.14 g) was added to a solution of sodium (2.0 g) in ethanol (30 ml), and the solution was refluxed by heating for 10 hours. The solvent was evaporated and the residue was added to ice water, which was extracted with chloroform, washed with water, dried and evaporated. The residue was purified by column chromatography on silica gel, to give 4-ethoxy-3-methoxy-2-methyl-pyridine (2.6 g) as a light brown oil.

Workup

  1. temperaturethe solution was refluxed
  2. temperatureby heating for 10 hours
  3. customThe solvent was evaporated
  4. additionthe residue was added to ice water, which
  5. extractionwas extracted with chloroform
  6. washwashed with water
  7. customdried
  8. customevaporated
  9. customThe residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-0833907527804ce6a54ae24e158f665d
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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