Potassium Carbonate → HCID 54352099, compound

HRID 564950Notes

Reaction equation

HRID 564950 reaction equation
Br[CH2:2][CH2:3][CH2:4][C:5]([NH:7][C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=1)=[O:6].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.C(OCC)(=O)C>[O:6]=[C:5]1[CH2:4][CH2:3][CH2:2][N:7]1[C:8]1[CH:20]=[CH:19][C:11]([CH:12]=[CH:13][C:14]([O:16][CH2:17][CH3:18])=[O:15])=[CH:10][CH:9]=1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 53881913HCID 53881913, compound

Product 1

HCID 54352099HCID 54352099, compoundYield 87.8%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of ethyl 4-(4-bromobutyramido)cinnamate (420 mg) in N,N-dimethylformamide (5 ml) was added potassium carbonate (552 mg) at ambient temperature and the resulting mixture was warmed at 50° C. for three hours. The reaction mixture was diluted with ethyl acetate and washed with water and brine. The organic phase was dried over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was purified by flash column chromatography eluting with chloroform to afford ethyl 4-(2-oxo-1-pyrrolidinyl)cinnamate (281 mg) as a pale yellow solid.

Workup

  1. washwashed with water and brine
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customThe residue was purified by flash column chromatography
  5. washeluting with chloroform

Sources & evidence

ORD record
ord-96fc1f3657524929afefec1e6869dbb0
Source dataset
uspto-grants-2001_01
Patent number
US06169095A

Reaction notes

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