Allyl bromide → HCID 19025017, compound

HRID 1033934Notes

Reaction equation

HRID 1033934 reaction equation
[CH3:1][C:2]1[CH2:6][N:5]([C:7]([CH3:12])([CH3:11])[C:8]([OH:10])=[O:9])[C:4](=[O:13])[C:3]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:26](Br)[CH:27]=[CH2:28]>C(#N)C>[CH3:1][C:2]1[CH2:6][N:5]([C:7]([CH3:11])([CH3:12])[C:8]([O:10][CH2:28][CH:27]=[CH2:26])=[O:9])[C:4](=[O:13])[C:3]=1[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

5

Reactant 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 19025021HCID 19025021, compound

Product 1

HCID 19025017HCID 19025017, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

1.5 g (5.8 mmol) of 2-(4-methyl-2-oxo-3-phenyl-3-pyrrolin-1-yl)isobutyric acid was dissolved in 50 ml of acetonitrile, and 0.83 g (6 mmol) of potassium carbonate and 0.73 g (6 mmol) of allyl bromide were added thereto. The mixture was refluxed under heating for 1 hour. After completion of the reaction, acetonitrile was distilled off, and ice water was added to the residue. The mixture was extracted with ethyl acetate. The extract was treated by a conventional method to obtain 1.7 g of a crude product. This crude product was purified by column chromatography to obtain 1.4 g (yield: 82%) of the desired product having a melting point of from 65° to 67° C.

Workup

  1. temperatureThe mixture was refluxed
  2. temperatureunder heating for 1 hour
  3. distillationwas distilled off
  4. additionice water was added to the residue
  5. extractionThe mixture was extracted with ethyl acetate
  6. additionThe extract was treated by a conventional method
  7. customto obtain 1.7 g of a crude product
  8. customThis crude product was purified by column chromatography

Sources & evidence

ORD record
ord-6b948750c6bb4e0abfffafa2de46fa7e
Source dataset
uspto-grants-1994_05
Patent number
US05312929

Reaction notes

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