Dimethyl Sulfoxide → 2-(Methoxymethyl)pyridine

HRID 1076368Notes

Reaction equation

HRID 1076368 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][OH:8].[H-].[Na+].[CH3:11]S(C)=O.CI>O>[CH3:11][O:8][CH2:7][C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6328Methyl iodideHCID 11474PiconolHCID 24758Sodium hydride

Product 1

HCID 2532202-(Methoxymethyl)pyridine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Also, 2-(methoxymethyl)pyridine is prepared by the following alternative procedure. A mixture of 10.9 g. of 2-pyridinemethanol and 2.4 g. of sodium hydride in 50 ml. of dimethylsulfoxide is warmed on a steam bath for 15 minutes, then cooled to room temperature. Methyl iodide (14.2 g.) is added and then the mixture is heated at 40°C. for 1 hour. Water (150 ml.) is then added and the mixture is extracted with ether. The extracts are dried, concentrated and distilled to give 2-(methoxymethyl)pyridine.

Workup

  1. customAlso, 2-(methoxymethyl)pyridine is prepared by the following alternative procedure
  2. additionA mixture of 10.9 g
  3. temperaturethe mixture is heated at 40°C. for 1 hour
  4. extractionthe mixture is extracted with ether
  5. customThe extracts are dried
  6. concentrationconcentrated
  7. distillationdistilled

Sources & evidence

ORD record
ord-32eb7d0517f8472b95086378f1ba2f01
Source dataset
uspto-grants-1976_05
Patent number
US03956494

Reaction notes

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