Methyl iodide → 2,6-Dichloro-4-(methoxymethyl)pyridine

HRID 651427Notes

Reaction equation

HRID 651427 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][OH:9])[CH:5]=[C:4]([Cl:10])[N:3]=1.[H-].[Na+].CI.[C:15](OCC)(=O)C>O1CCCC1>[Cl:1][C:2]1[CH:7]=[C:6]([CH2:8][O:9][CH3:15])[CH:5]=[C:4]([Cl:10])[N:3]=1

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 8857Ethyl AcetateHCID 24758Sodium hydrideHCID 2794840(2,6-Dichloropyridin-4-yl)methanol

Product 1

HCID 155502332,6-Dichloro-4-(methoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

0.18 g of 2,6-dichloro-4-pyridinemethanol were dissolved into 5 ml of tetrahydrofuran (hereinafter referred to as “THF”), the solution was cooled by ice, and thereafter 0.04 g of sodium hydride (oil base, 60%) were added. To this, a solution of 0.15 g of methyl iodide dissolved in 2 ml of THF was added dropwise, and stirring was conducted for 2 hours at room temperature. Ethyl acetate was added to the reacted solution, and after the organic phase was washed by water, the organic phase was dried by adding sodium sulfate. The solvent was removed by evaporation, and the residue was purified by silica gel column chromatography to obtain 0.06 g of 2,6-dichloro-4-methoxymethylpyridine (Compound No. 1).

Workup

  1. temperaturewas cooled by ice
  2. additionwas added dropwise
  3. washafter the organic phase was washed by water
  4. customthe organic phase was dried
  5. additionby adding sodium sulfate
  6. customThe solvent was removed by evaporation
  7. customthe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-3347a39eab45476b9e8f518207fd1a9d
Source dataset
uspto-grants-2001_08
Patent number
US06281231B1

Reaction notes

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