Ethyl cyanoacetate → Ethyl 1-cyanocyclopropanecarboxylate

HRID 2366730Notes

Reaction equation

HRID 2366730 reaction equation
[CH2:1]([O:3][C:4](=[O:8])[CH2:5][C:6]#[N:7])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:16][CH2:17]Br>CC(C)=O>[C:6]([C:5]1([C:4]([O:3][CH2:1][CH3:2])=[O:8])[CH2:17][CH2:16]1)#[N:7]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetate2×HCID 78391,2-Dibromoethane2×HCID 11430Potassium Carbonate

Product 1

HCID 380810Ethyl 1-cyanocyclopropanecarboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Ethylcyanoacetate (15.0 mL, 141 mmol) was added to a mixture of potassium carbonate (48.7 g, 353 mmol) and acetone (200 mL), and 1,2-dibromoethane (13.4 mL, 155 mmol) was added dropwise to the resulting mixture over a period of eight minutes. The reaction was heated at reflux overnight. An analysis by TLC indicated the presence of ethylcyanoacetate, and additional 1,2-dibromoethane (1.8 mL, 0.15 equivalent) was added. The reaction mixture was heated at reflux for an additional four hours and filtered through a layer of CELITE filter agent. The filter cake was washed with acetone (200 mL), and the combined filtrates were concentrated under reduced pressure to provide ethyl 1-cyanocyclopropanecarboxylate as an orange oil containing about 10 mole % 1,2-dibromoethane.

Workup

  1. additionwas added dropwise to the resulting mixture over a period of eight minutes
  2. temperatureThe reaction was heated
  3. temperatureat reflux overnight
  4. additionwas added
  5. temperatureThe reaction mixture was heated
  6. temperatureat reflux for an additional four hours
  7. filtrationfiltered through a layer of CELITE filter agent
  8. washThe filter cake was washed with acetone (200 mL)
  9. concentrationthe combined filtrates were concentrated under reduced pressure

Sources & evidence

ORD record
ord-34c939d804b849be8a2accc55f1e49fb
Source dataset
uspto-grants-2014_04
Patent number
US08697873B2

Reaction notes

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