Methyl iodide → HCID 21915915, compound

HRID 1659133Notes

Reaction equation

HRID 1659133 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]([OH:9])[CH3:8].[H-].[Na+].[CH3:12]I>CS(C)=O>[CH3:12][O:9][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[CH3:8]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 86784alpha-Methyl-2-pyridinemethanol

Product 1

HCID 21915915HCID 21915915, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
20 °C

Procedure

To a stirred solution of 223 g. of 1-(2-pyridyl)-ethanol in 1500 ml. of dry dimethylsulfoxide is added 2.3 moles of sodium hydride in portions, under nitrogen, maintaining the temperature at 20°C. After two hours, 331 g. of methyl iodide is added at 20°C. After stirring for another 3 hours, the mixture is poured onto ice-water and extracted three times with ether. The organic phase is washed with water, dried over magnesium sulfate, concentrated in vacuo, and the residue is distilled to give 2-(1-methoxyethyl)pyridine.

Workup

  1. additionthe mixture is poured onto ice-water
  2. extractionextracted three times with ether
  3. washThe organic phase is washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. distillationthe residue is distilled

Sources & evidence

ORD record
ord-04c511a6fc0c4ed082c6fcfee01387d1
Source dataset
uspto-grants-1976_06
Patent number
US03966945

Reaction notes

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