Methyl cyanoacetate → Methyl 1-cyanocyclopentane-1-carboxylate

HRID 2234513Notes

Reaction equation

HRID 2234513 reaction equation
[C:1]([CH2:3][C:4]([O:6][CH3:7])=[O:5])#[N:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:15][CH2:16][CH2:17][CH2:18]Br>CN(C=O)C>[CH3:7][O:6][C:4]([C:3]1([C:1]#[N:2])[CH2:18][CH2:17][CH2:16][CH2:15]1)=[O:5]

Participants

5

Reactant 3

HCID 7747Methyl cyanoacetateHCID 80561,4-DibromobutaneHCID 11430Potassium Carbonate

Product 1

HCID 22736532Methyl 1-cyanocyclopentane-1-carboxylate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Methyl cyanoacetate (Fluka; 25 g, 252.3 mmol) and potassium carbonate (83.7 g, 605.5 mmol) were stirred in DMF (250 mL). 1,4-Dibromobutane (Aldrich; 30.1 mL, 252.3 mmol) was slowly added. This caused and exotherm that continued after the addition was completed and a water bath was used to prevent the temperature exceeding 90° C. The mixture slowly cooled to ambient temperature and was stirred overnight and then heated at 75° C. for 3 hours.

Workup

  1. additionafter the addition
  2. customa water bath was used
  3. customexceeding 90° C
  4. temperatureheated at 75° C. for 3 hours

Sources & evidence

ORD record
ord-35068bd6489f4f70b2bb5d31ea65c315
Source dataset
uspto-grants-2010_05
Patent number
US07709471B2

Reaction notes

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