Acetic Acid → Diethyl 3-ethyl-5-oxo-2,2-pyrrolidinedicarboxylate

HRID 398300Notes

Reaction equation

HRID 398300 reaction equation
[Na].[C:2]([NH:5][CH:6]([C:12]([O:14][CH2:15][CH3:16])=[O:13])[C:7]([O:9][CH2:10][CH3:11])=[O:8])(=[O:4])[CH3:3].C(O[C:20](=O)/[CH:21]=[CH:22]/CC)C.C(O)(=O)C>C(O)C>[CH2:10]([O:9][C:7]([C:6]1([C:12]([O:14][CH2:15][CH3:16])=[O:13])[CH:20]([CH2:21][CH3:22])[CH2:3][C:2](=[O:4])[NH:5]1)=[O:8])[CH3:11]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 14041Acetamidomalonic acid diethyl esterHCID 5360545SodiumHCID 5367761Ethyl trans-2-pentenoate

Product 1

HCID 255944Diethyl 3-ethyl-5-oxo-2,2-pyrrolidinedicarboxylateYield 87.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 150 mg of sodium dissolved in 150 mL of absolute ethanol was added diethyl acetamidomalonate (5.3 g, 25 mmol) and ethyl-(2E)-pent-2-enoate (3.5 g, 27.3 mmol). The reaction mixture was then refluxed for 20 h. After this period of time, 2 mL of glacial acetic acid was added, volatiles were removed under pressure with the aid of a water aspirator and heating bath. On cooling the residue solidified. The residue was dissolved in 50 mL of toluene and to this was added 20 mL of petroleum ether. The product precipitated when the mixture was cooled. The crystals were collected and washed with water and further dried in vacuo to obtain a white solid (5.6 g, 79.77%). Mass Spectrum (+ESI): 258 (M+H)+.

Workup

  1. temperatureThe reaction mixture was then refluxed for 20 h
  2. customvolatiles were removed under pressure with the aid of a water aspirator
  3. temperatureheating bath
  4. temperatureOn cooling the residue solidified
  5. dissolutionThe residue was dissolved in 50 mL of toluene
  6. additionto this was added 20 mL of petroleum ether
  7. customThe product precipitated when the mixture
  8. temperaturewas cooled
  9. customThe crystals were collected
  10. washwashed with water
  11. customfurther dried in vacuo

Sources & evidence

ORD record
ord-b5ab014544dc499db845b4e00332b6e7
Source dataset
uspto-grants-2003_08
Patent number
US06610734B2

Reaction notes

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