Propanedioic acid, 2-[2-(2-pyridinyl)ethyl]-, 1,3-diethyl ester → 4-(Pyridin-2-yl)butanoic acid

HRID 1900590Notes

Reaction equation

HRID 1900590 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH:9](C(OCC)=O)[C:10]([O:12]CC)=[O:11]>C(O)C.[OH-].[Na+]>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][CH2:8][CH2:9][C:10]([OH:12])=[O:11]

Participants

4

Reactant 1

HCID 15591894Propanedioic acid, 2-[2-(2-pyridinyl)ethyl]-, 1,3-diethyl ester

Product 1

HCID 137371714-(Pyridin-2-yl)butanoic acidYield 77.3%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of diethyl β-(2-pyridyl)-ethylmalonate (25 g, 94 mmol) in ethanol (100 mL) and NaOH (1M, 200 mL) was refluxed for 2 hours. The ethanol was removed by distillation, and the solution was acidified with concentrated H2SO4. The resulting solution was refluxed for 30 minutes, and then the pH was adjusted to 4. The solvent was removed and the residue was dried under vacuum. The residue was suspended in ethanol and filtered. The ethanol was removed to yield 4-(2-pyridyl)butanoic acid (46) (12 g).

Workup

  1. customThe ethanol was removed by distillation
  2. temperatureThe resulting solution was refluxed for 30 minutes
  3. customThe solvent was removed
  4. customthe residue was dried under vacuum
  5. filtrationfiltered
  6. customThe ethanol was removed

Sources & evidence

ORD record
ord-00a521fd10b549be8faf3bd3be081d8e
Source dataset
uspto-grants-1996_11
Patent number
US05576315

Reaction notes

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