Ethyl Acetoacetate → Ethyl 1-acetylcyclopropane-1-carboxylate

HRID 1954632Notes

Reaction equation

HRID 1954632 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].Br[CH:11](Br)[CH3:12].C(=O)([O-])[O-].[K+].[K+]>CC(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 8868Ethyl AcetoacetateHCID 112011,1-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 65.1%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethyl acetoacetate (100 g, 0.77 mol) was dissolved in acetone (500 ml). To the thus obtained solution was added dibromoethane (361 g, 1.92 mol) and potassium carbonate (266 g, 1.92 mol) and the mixture was heated under reflux for 4 days. After filtering off insoluble matter, the filtrate was distilled under reduced pressure (80° C./8 mmHg) to obtain 78.1 g (65.1%) of the title compound as a colorless oily substance.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4 days
  3. filtrationAfter filtering off insoluble matter
  4. distillationthe filtrate was distilled under reduced pressure (80° C./8 mmHg)

Sources & evidence

ORD record
ord-f0dca3497ab24a46ae45a99c7ccac80e
Source dataset
uspto-grants-2000_09
Patent number
US06121285

Reaction notes

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