Methyl acetoacetate → Methyl 1-acetylcyclopropane-1-carboxylate

HRID 1790876Notes

Reaction equation

HRID 1790876 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].C(=O)([O-])[O-].[K+].[K+].Br[CH:16](Br)[CH3:17]>CC(C)=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:4]1([C:5](=[O:6])[CH3:7])[CH2:17][CH2:16]1)=[O:8]

Participants

6

Reactant 3

HCID 7757Methyl acetoacetateHCID 112011,1-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 10214400Methyl 1-acetylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

56 g of acetoacetic acid methyl ester 3 is dissolved in 500 ml of acetone, and 276.2 g of potassium carbonate as well as 86 ml of dibromoethane are added while being cooled with ice. It is heated under nitrogen to 50° C. and stirred for 72 hours at this temperature. After cooling, the mixture is diluted with ethyl acetate, washed with water and saturated sodium chloride solution, dried on sodium sulfate and concentrated by evaporation. The residue is distilled in a vacuum, whereby 66 g of the title compound is obtained as a colorless oil.

Workup

  1. temperaturewhile being cooled with ice
  2. temperatureAfter cooling
  3. washwashed with water and saturated sodium chloride solution
  4. customdried on sodium sulfate
  5. concentrationconcentrated by evaporation
  6. distillationThe residue is distilled in a vacuum

Sources & evidence

ORD record
ord-288b99af453e4009bbf2075cf217e681
Source dataset
uspto-grants-2006_07
Patent number
US07071344B1

Reaction notes

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