Water → HCID 21486893, compound

HRID 1659127Notes

Reaction equation

HRID 1659127 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][C:8]#[N:9].[H-].[Na+].[CH3:12][O:13][CH2:14]Cl.O>CS(C)=O>[CH3:12][O:13][CH2:14][CH:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)[C:8]#[N:9]

Participants

6

Reactant 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 75959Pyridine-2-acetonitrile

Product 1

HCID 21486893HCID 21486893, compound

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a stirred solution of 11.8 g. (0.1 mole) of 2-pyridylacetonitrile in dry dimethylsulfoxide at 10°C. is added 0.1 mole of sodium hydride (dispersed in mineral oil). After 20 minutes, 0.1 mole of chloromethyl methyl ether is added with cooling and the mixture is kept at 10°C. for 2 hours, then allowed to warm to room temperature overnight. The reaction mixture is poured into water and extracted with ether. The organic phase is washed with water, dried over anhydrous sodium sulfate, concentrated under vacuum and distilled to give 3-methoxy-2-(2-pyridyl)propionitrile.

Workup

  1. temperaturewith cooling
  2. waitthe mixture is kept at 10°C. for 2 hours
  3. extractionextracted with ether
  4. washThe organic phase is washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated under vacuum
  7. distillationdistilled

Sources & evidence

ORD record
ord-ff609fe94f464d07a89dc738d565e56b
Source dataset
uspto-grants-1976_06
Patent number
US03966945

Reaction notes

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