Ethyl Acetoacetate → Ethyl 1-acetylcyclopropane-1-carboxylate

HRID 635107Notes

Reaction equation

HRID 635107 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-f96f694e8cd24e8798f9f5d1b7aab2ef
Source dataset
uspto-grants-2001_02
Patent number
US06184388B2

Reaction notes

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