Hydrochloric Acid → Diethyl 2-[2-(4-pyridyl)ethyl]malonate

HRID 478731Notes

Reaction equation

HRID 478731 reaction equation
[C:1]([O:9][CH2:10][CH3:11])(=[O:8])[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[O-]CC.[Na+].[CH:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=[CH2:17].Cl>C(O)C.O>[N:21]1[CH:22]=[CH:23][C:18]([CH2:16][CH2:17][CH:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])[C:1]([O:9][CH2:10][CH3:11])=[O:8])=[CH:19][CH:20]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 75024-VinylpyridineHCID 7761Diethyl MalonateHCID 2723922Sodium ethoxide

Product 1

HCID 2801722Diethyl 2-[2-(4-pyridyl)ethyl]malonateYield 46.4%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a solution of diethyl malonate (9.6 g, 0.06mol) in 20 ml of absolute ethanol was added sodium ethoxide (4.1 g) portionwise at room temperature while stirring and the mixture was further stirred for 4 hours followed by dropwise addition of 4-vinylpyridine (2.1 g, 0.02 mol). The mixture was then stirred overnight. Evaporation of ethanol under reduced pressure gave a residue to which was added water followed by neutralization with 3N hydrochloric acid. The mixture was extracted with ethyl acetate. The extracted liquid was treated according to conventional techniques. Evaporation of solvent yielded a residue which was subjected to purification using column chromatography on silica gel to afford diethyl 2-(pyridin-4-yl)ethylmalonate as an oil (2.46 g, 46%).

Workup

  1. stirringthe mixture was further stirred for 4 hours
  2. stirringThe mixture was then stirred overnight
  3. customEvaporation of ethanol under reduced pressure
  4. customgave a residue to which
  5. extractionThe mixture was extracted with ethyl acetate
  6. additionThe extracted liquid was treated
  7. customEvaporation of solvent
  8. customyielded a residue which
  9. customwas subjected to purification

Sources & evidence

ORD record
ord-3fd7aff3488a4b779d372f39f9aa82c0
Source dataset
uspto-grants-2003_11
Patent number
US06642250B2

Reaction notes

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