1,2-Dibromoethane → Ethyl 1-acetylcyclopropane-1-carboxylate

HRID 1939266Notes

Reaction equation

HRID 1939266 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].Br[CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[C:3]([C:2]1([C:1]([O:7][CH2:8][CH3:9])=[O:6])[CH2:12][CH2:11]1)(=[O:4])[CH3:5]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 8868Ethyl AcetoacetateHCID 11430Potassium Carbonate

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 60.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 10.4 g of ethyl acetoacetate, 15 g of 1,2-dibromoethane, 23 g of potassium carbonate, and 150 ml of N,N-dimethylformamide (DMF) was stirred at room temperature for 2 days. An insoluble material was removed by filtration, and the filtrate was concentrated to dryness under reduced pressure. Water was added to the residue, and the mixture was extracted with chloroform. The extract was dried over anhydrous sodium sulfate, and the solvent was removed under reduced pressure. The resulting pale yellow oily substance was distilled under reduced pressure to give 7.5 g of ethyl 1-acetyl-1-cyclopropanecarboxylate as a fraction having a boiling point of 70° to 71° C./2-3 mmHg.

Workup

  1. customAn insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated to dryness under reduced pressure
  3. additionWater was added to the residue
  4. extractionthe mixture was extracted with chloroform
  5. dry with materialThe extract was dried over anhydrous sodium sulfate
  6. customthe solvent was removed under reduced pressure
  7. distillationThe resulting pale yellow oily substance was distilled under reduced pressure

Sources & evidence

ORD record
ord-b35e356cede64fc29e76417174e237ca
Source dataset
uspto-grants-1997_12
Patent number
US05696132

Reaction notes

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