Ethanol → 5-(Ethoxymethyl)picolinonitrile

HRID 1025286Notes

Reaction equation

HRID 1025286 reaction equation
CS([O:5][CH2:6][C:7]1[CH:8]=[N:9][C:10]([C:13]#[N:14])=[CH:11][CH:12]=1)(=O)=O.[CH3:15][CH2:16]O>>[CH2:15]([O:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]#[N:14])=[N:9][CH:8]=1)[CH3:16]

Participants

3

Reactant 2

HCID 702EthanolHCID 46901655HCID 46901655, compound

Product 1

HCID 670860605-(Ethoxymethyl)picolinonitrile

Procedure

(6-Cyanopyridin-3-yl)methyl methanesulfonate (199 mg, 0.94 mmol) in 2 mL anhydrous EtOH was heated at 85° C. in a sealed tube for 3.5 h. The mixture was concentrated and purified by silica gel chromatography (elution with 0-25% EtOAc/Hex) to afford 5-(ethoxymethyl)picolinonitrile (104 mg).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by silica gel chromatography (elution with 0-25% EtOAc/Hex)

Sources & evidence

ORD record
ord-0f2b3ec2ac424c3a9666747ef33c3896
Source dataset
uspto-grants-2014_05
Patent number
US08729071B2

Reaction notes

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