Ethyl benzoylacetate → HCID 13969923, compound

HRID 392596Notes

Reaction equation

HRID 392596 reaction equation
[C:1]([CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:15](Br)[CH2:16]Br.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[C:1]([C:9]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:16][CH2:15]1)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 13969923HCID 13969923, compoundYield 68.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 1370 ml of acetonitrile were added ethyl benzoylacetate (49.9 g, 0.26 mol), 1,2-dibromomethane (48.8 g, 0.26 g) and anhydrous potassium carbonate (143.6 g, 1.04 mol) and the mixture was stirred under reflux for 18 h. After cooling, the reaction mixture was filtrated and concentrated. The residual solution (56.3 g) was purified by silica gel column chromatography (ethyl acetate/hexane=1/5) to give the title compound (38.7 g) as a colorless oil (yield 68%).

Workup

  1. temperatureunder reflux for 18 h
  2. temperatureAfter cooling
  3. filtrationthe reaction mixture was filtrated
  4. concentrationconcentrated
  5. customThe residual solution (56.3 g) was purified by silica gel column chromatography (ethyl acetate/hexane=1/5)

Sources & evidence

ORD record
ord-027ddca303904656acc5bedbfe554cf3
Source dataset
uspto-grants-2004_10
Patent number
US06800778B1

Reaction notes

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