Water → 5-Methoxy-2-methylpyridine

HRID 1720365Notes

Reaction equation

HRID 1720365 reaction equation
[H-].[Na+].[OH:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1.[CH3:11]I.O>CN(C=O)C>[CH3:11][O:3][C:4]1[CH:5]=[CH:6][C:7]([CH3:10])=[N:8][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 142752-Methyl-5-hydroxypyridineHCID 24758Sodium hydride

Product 1

HCID 133587775-Methoxy-2-methylpyridineYield 39.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (3.6 g, 150 mmol) was added portionwise to 5-hydroxy-2-picoline (15.0 g, 137 mmol) in DMF (120 mL). After 30 min., CH3I (10.2 mL, 156 mmol) was added and the mixture stirred 2 hours at r.t. Water was added and the compound was extracted with Et2O (3×). The organic extracts were washed with brine (2×), dried over Na2SO4 and concentrated in vacuo to give 6.7 g of the title compound.

Workup

  1. extractionthe compound was extracted with Et2O (3×)
  2. washThe organic extracts were washed with brine (2×)
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-366cf30bec7a41229231d76deed7c27a
Source dataset
uspto-grants-1996_04
Patent number
US05506227

Reaction notes

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