Triethylamine → Methyl 4-(3-pyridyl)butyrate

HRID 478730Notes

Reaction equation

HRID 478730 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH2:13]C#N)=[O:11])[CH:2]=1.C(N(CC)CC)C>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])[CH:2]=1

Participants

4

Reactant 2

HCID 8471TriethylamineHCID 18002651Cyanomethyl 4-(pyridin-3-yl)butanoate

Product 1

HCID 152209Methyl 4-(3-pyridyl)butyrateYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of cyanomethyl 4-(pyridin-3-yl)butanoate (0.57 g, 2.81 mmol) and triethylamine (57 mg, 0.56 mmol) in dry methanol (10 ml) was heated under reflux overnight, and evaporated to give a residue. The resultant residue was subjected to purification using column chromatography on silica gel to afford a target product, methyl 4-(pyridin-3-yl)butanoate (0.46 g, 92%).

Workup

  1. temperaturewas heated
  2. temperatureunder reflux overnight
  3. customevaporated
  4. customto give a residue
  5. customThe resultant residue was subjected to purification

Sources & evidence

ORD record
ord-22bd27c3d64d4d87b0f6a521bae7b4a8
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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