Sodium Iodide → Propan-2-yl 4-oxo-4-phenylbut-2-enoate

HRID 1981871Notes

Reaction equation

HRID 1981871 reaction equation
[C:1]([CH:9]=[CH:10][C:11]([OH:13])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:14](Br)([CH3:16])[CH3:15].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+]>CN(C)C=O.O>[C:1]([CH:9]=[CH:10][C:11]([O:13][CH:14]([CH3:16])[CH3:15])=[O:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 63582-BromopropaneHCID 11430Potassium CarbonateHCID 94714Beta-benzoylacrylic acid

Product 1

HCID 54289570Propan-2-yl 4-oxo-4-phenylbut-2-enoate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3.52 g of 3-benzoylacrylic acid in 30 ml of dimethylformamide were added 8 ml of isopropylbromide, 5.5 g of potassium carbonate and a catalystic amount of sodium iodide. The mixture was stirred at room temperature for 4 hours and allowed to stand overnight. To the reaction solution was added water, the mixture was extracted with diethyl ether, and the diethyl ether layer was washed with water and dried over magnesium sulfate. The diethyl ether was removed from the solution by evaporation, and the residue was purified by silica gel column chromatography using a mixture of hexane and diethyl ether as an eluent to give 2.27 g of isopropyl 3-benzoylacrylate as an oil.

Workup

  1. waitto stand overnight
  2. extractionthe mixture was extracted with diethyl ether
  3. washthe diethyl ether layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customThe diethyl ether was removed from the solution by evaporation
  6. customthe residue was purified by silica gel column chromatography
  7. additiona mixture of hexane and diethyl ether as an eluent

Sources & evidence

ORD record
ord-a5e70c8a8d9049f9a7c1edcbff2fb899
Source dataset
uspto-grants-1986_06
Patent number
US04594197

Reaction notes

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