Ethyl benzoylacetate → Ethyl 2-benzoyl-5-oxo-5-phenylvalerate

HRID 1440790Notes

Reaction equation

HRID 1440790 reaction equation
Cl.CN(C)[CH2:4][CH2:5][C:6]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7].[C:15]([CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[O-]CC.[Na+]>C(O)C>[C:15]([CH:23]([CH2:4][CH2:5][C:6](=[O:7])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:24]([O:26][CH2:27][CH3:28])=[O:25])(=[O:22])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 928441-Propanone, 3-(dimethylamino)-1-phenyl-, hydrochloride (1:1)HCID 2723922Sodium ethoxide

Product 1

HCID 12015084Ethyl 2-benzoyl-5-oxo-5-phenylvalerateYield 75.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred mixture of 2.14 g of β-dimethylaminopropiophenone hydrochloride and 1.92 g of ethyl benzoylacetate in 30 cc of ethanol was added in small portions 1.36 g of sodium ethoxide at room temperature. The resulting mixture was stirred at room temperature for 30 minutes and then heated under reflux for 1 hour. After cooling, the solvent was distilled off and water was added to the residue. The aqueous layer was acidified with 1N HCl, and extracted twice with chloroform. The combined organic layer was washed with a saturated aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was distilled off and the crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/5) to obtain 2.45 g of compound G. Yield: 75.5%.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1 hour
  3. temperatureAfter cooling
  4. distillationthe solvent was distilled off
  5. additionwater was added to the residue
  6. extractionextracted twice with chloroform
  7. washThe combined organic layer was washed with a saturated aqueous sodium chloride solution
  8. dry with materialdried over magnesium sulfate
  9. distillationThe solvent was distilled off
  10. customthe crude product thus obtained
  11. customwas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-3fc5d7a537e94d67b7eeb24fcf6ed66e
Source dataset
uspto-grants-1996_03
Patent number
US05500424

Reaction notes

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