Diethyl 2-[2-(4-pyridyl)ethyl]malonate → Methyl 4-(Pyridin-4-yl)butanoate

HRID 1900591Notes

Reaction equation

HRID 1900591 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH:9](C(OCC)=O)[C:10]([O:12][CH2:13]C)=[O:11])=[CH:3][CH:2]=1>C(O)C.[OH-].[Na+]>[N:1]1[CH:6]=[CH:5][C:4]([CH2:7][CH2:8][CH2:9][C:10]([O:12][CH3:13])=[O:11])=[CH:3][CH:2]=1

Participants

4

Reactant 1

HCID 2801722Diethyl 2-[2-(4-pyridyl)ethyl]malonate

Product 1

HCID 12114953Methyl 4-(Pyridin-4-yl)butanoateYield 89%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of diethyl β-(4-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 the pH was adjusted to 4. The solvent was removed and the residue was dried under vacuum. The residue was taken up in methanol (300 mL), trimethyl orthoformate (10 mL) and H2SO4 (5 mL), and the resulting solution was refluxed for 3 hours. The solvent was removed, and the residue was taken up in CHCl3 and extracted with NaOH (1M) and saturated brine, dried (Na2SO4) and evaporated to yield methyl 4-(4-pyridyl)butanoate (48) (15 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. temperaturetrimethyl orthoformate (10 mL) and H2SO4 (5 mL), and the resulting solution was refluxed for 3 hours
  6. customThe solvent was removed
  7. extractionextracted with NaOH (1M) and saturated brine
  8. dry with materialdried (Na2SO4)
  9. customevaporated

Sources & evidence

ORD record
ord-8e6ebd2c9ab84f4e948fd4199de4987d
Source dataset
uspto-grants-1996_11
Patent number
US05576315

Reaction notes

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