Methyl acetoacetate → Methyl 1-acetylcyclopropane-1-carboxylate

HRID 83581Notes

Reaction equation

HRID 83581 reaction equation
[C:1]([O:7][CH3:8])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17]Br>CC(C)=O>[CH3:8][O:7][C:1]([C:2]1([C:3](=[O:4])[CH3:5])[CH2:17][CH2:16]1)=[O:6]

Participants

5

Reactant 3

HCID 7757Methyl acetoacetateHCID 78391,2-DibromoethaneHCID 11430Potassium Carbonate

Product 1

HCID 10214400Methyl 1-acetylcyclopropane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of methyl acetoacetate (3 ml) in acetone (30 ml) were sequentially added potassium carbonate (11.54 g) and 1,2-dibromoethane (2.4 ml) at room temperature, and the mixture was stirred at 65° C. for 17 hours. This reaction mixture was filtered, the filtrate was concentrated under reduced pressure, and the resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1) to give the titled compound (2.17 g).

Workup

  1. customat room temperature
  2. filtrationThis reaction mixture was filtered
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customthe resulting residue was purified by silica gel column chromatography (eluent: n-hexane/ethyl acetate=10/1)

Sources & evidence

ORD record
ord-6de4f53d1c7c4a7686de67513f7896dc
Source dataset
uspto-grants-2014_09
Patent number
US08846746B2

Reaction notes

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