Water → HCID 86618355, compound

HRID 1441701Notes

Reaction equation

HRID 1441701 reaction equation
[H-].[Na+].[C:3]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[Br:17][C:18]([CH2:20]Br)=[CH2:19].O>CN(C=O)C.C(OCC)(=O)C>[C:3]([CH:11]([CH2:20][C:18]([Br:17])=[CH2:19])[C:12]([O:14][CH2:15][CH3:16])=[O:13])(=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

7

Reactant 4

HCID 962WaterHCID 7170Ethyl benzoylacetateHCID 105522,3-DibromopropeneHCID 24758Sodium hydride

Product 1

HCID 86618355HCID 86618355, compoundYield 86.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Sodium hydride (0.26 g, 6.0 mmol) was added under ice cooling to a solution (10 ml) of ethyl benzoylacetate (1.0 ml, 5.77 mmol) in DMF, followed by stirring for 30 minutes, and then 2,3-dibromopropene (0.63 ml, 5.77 mmol) was added. The resulting mixture was stirred at room temperature for 1.5 hours, water was added to the reaction mixture, and extraction with ethyl acetate was performed three times. The organic layer was dried over anhydrous sodium sulfate, the solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1). The solvent was distilled off under reduced pressure, to thereby obtain 1.55 g (yield: 86%) of ethyl 2-benzoyl-4-bromo-4-pentenoate as a colorless oil.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1.5 hours
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. distillationthe solvent was distilled off under reduced pressure
  4. customthe residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=4/1)
  5. distillationThe solvent was distilled off under reduced pressure

Sources & evidence

ORD record
ord-0cdba053b0f74248b9dcb69756cd2e13
Source dataset
uspto-grants-2010_02
Patent number
US07655680B2

Reaction notes

Loading…