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

HRID 1366493Notes

Reaction equation

HRID 1366493 reaction equation
[O:1]=[C:2]([CH3:9])[CH2:3][C:4]([O:6][CH2:7][CH3:8])=[O:5].Br[CH2:11][CH2:12]Br.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O>[C:2]([C:3]1([C:4]([O:6][CH2:7][CH3:8])=[O:5])[CH2:12][CH2:11]1)(=[O:1])[CH3:9]

Participants

6

Reactant 3

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

Product 1

HCID 234183Ethyl 1-acetylcyclopropane-1-carboxylateYield 52.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of ethyl 3-oxobutanoate (10 mL, 78.45 mmol) and 1,2-dibromoethane (6.5 mL, 78.45 mmol) in 150 mL of DMF was added potassium carbonate (22.7 g, 164.74 mmol). The resulting reaction mixture was stirred at room temperature for 2 days. The solution was diluted with 300 mL of water. The product was extracted into diethyl ether (2×200 mL), and the combined organic extracts were washed with water (1×1000 mL), and dried (MgSO4). Filtration and atmospheric distillation of the ether provided the crude product, which was distilled under reduced pressure (10 mBar) to provide ethyl 1-acetylcyclopropanecarboxylate (6.4273 g, 52%). LCMS: (M+H)+: not detected.

Workup

  1. customThe resulting reaction mixture
  2. extractionThe product was extracted into diethyl ether (2×200 mL)
  3. washthe combined organic extracts were washed with water (1×1000 mL)
  4. dry with materialdried (MgSO4)
  5. filtrationFiltration and atmospheric distillation of the ether
  6. customprovided the crude product, which
  7. distillationwas distilled under reduced pressure (10 mBar)

Sources & evidence

ORD record
ord-bf1b3b33a5294552953a55319f17b9c5
Source dataset
uspto-grants-2011_02
Patent number
US07893056B2

Reaction notes

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