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

HRID 1613555Notes

Reaction equation

HRID 1613555 reaction equation
[C:1]([O:7][CH2:8][CH3:9])(=[O:6])[CH2:2][C:3]([CH3:5])=[O:4].Br[CH2:11][CH2:12]Br.[OH-].[K+]>CS(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 78391,2-DibromoethaneHCID 8868Ethyl AcetoacetateHCID 14797Potassium Hydroxide

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 104%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A mixture of ethyl acetoacetate (13.0 g, 99.9 mmol), 1,2-dibromoethane (13 mL, 151 mmol) and potassium hydroxide (14.0 g, 250 mmol) in dimethylsulfoxide (130 mL) was stirred at ambient temperature overnight. The mixture was poured into ice water and extracted with diethyl ether. The combined organic layers were washed with brine, and dried over sodium sulfate. Filtration and concentration gave 16.22 g of an oily material, which was purified by column chromatography (silica gel 80 g, 20% ethyl acetate in n-hexane) to give 12.97 g (83.1%) of 1, as a pale yellow oil.

Workup

  1. extractionextracted with diethyl ether
  2. washThe combined organic layers were washed with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationFiltration and concentration

Sources & evidence

ORD record
ord-0bba595c7e7d40c69423cb9492cedf7b
Source dataset
uspto-grants-1993_03
Patent number
US05194431

Reaction notes

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