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

HRID 478732Notes

Reaction equation

HRID 478732 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>Cl>[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

3

Reactant 1

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

Product 1

HCID 12114953Methyl 4-(Pyridin-4-yl)butanoate

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of diethyl 2-(pyridin-4-yl)ethylmalonate (2.4 g, 0.009 mol) and 30 ml of conc. hydrochloric acid was heated at 100° C. for 15 hours and an excess amount of hydrochloric acid was then evaporated under reduced pressure. A mixture of the resultant residue and 10% hydrochloric acid-methanol solution was heated under reflux, evaporated, neutralized with saturated aqueous sodium hydrogen carbonate, and extracted with ethyl acetate. The extract was treated according to conventional techniques. Evaporation of solvent yielded the title compound, methyl 4-(pyridin-4-yl)butanoate, as an oil (0.62 g, 39%).

Workup

  1. customan excess amount of hydrochloric acid was then evaporated under reduced pressure
  2. additionA mixture of the resultant residue and 10% hydrochloric acid-methanol solution
  3. temperaturewas heated
  4. temperatureunder reflux
  5. customevaporated
  6. extractionextracted with ethyl acetate
  7. additionThe extract was treated
  8. customEvaporation of solvent

Sources & evidence

ORD record
ord-724b5cfdacff47dd9ea7e35d7682e1f2
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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