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

HRID 1969405Notes

Reaction equation

HRID 1969405 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18]Br>CC(C)=O>[C:2]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:18][CH2:17]1)(=[O:1])[CH3:9]

Participants

5

Reactant 3

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

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 60%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 3-oxobutanoate (26 g, 200 mmol) in acetone (500 mL) was added potassium carbonate (82.8 g, 600 mmol) followed by 1,2-dibromoethane (45.12 g, 240 mmol). The reaction was refluxed for 24 hrs, then the reaction mixture was filtered. The filtrate was concentrated in vacuo, and the residue was purified by a silica gel column chromatography (1:50(v/v) EtOAc/n-hexane) to afford the title compound as colorless oil (18.7 g, 60%).

Workup

  1. temperatureThe reaction was refluxed for 24 hrs
  2. filtrationthe reaction mixture was filtered
  3. concentrationThe filtrate was concentrated in vacuo
  4. customthe residue was purified by a silica gel column chromatography (1:50(v/v) EtOAc/n-hexane)

Sources & evidence

ORD record
ord-975b80a1e85343108c0e2b6ad5851331
Source dataset
uspto-grants-2013_04
Patent number
US08426585B2

Reaction notes

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