Ethyl cyanoacetate → HCID 86667498, compound

HRID 1978166Notes

Reaction equation

HRID 1978166 reaction equation
[Na:1].[C:2]([CH2:4][C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:3].[F:10][C:11]([F:18])([F:17])[C:12](OCC)=[O:13]>C(O)C>[Na:1].[C:2]([C:4](=[C:12]([OH:13])[C:11]([F:18])([F:17])[F:10])[C:5]([O:7][CH2:8][CH3:9])=[O:6])#[N:3]

Participants

5

Reactant 3

HCID 7764Ethyl cyanoacetateHCID 9794Ethyl trifluoroacetateHCID 5360545Sodium

Product 1

HCID 86667498HCID 86667498, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution obtained by dissolving 24.0 g (1.04 mol) of sodium metal in 400 ml of ethanol, 113.1 g (1.00 mol) of ethyl cyanoacetate was dropwise added with stirring at the room temperature. After stirring for one hour, 150.0 g (1.05 mol) of ethyl trifluoroacetate was dropwise added to the reaction mixture and stirred for 3 hours at the same temperature. After finishing the reaction, the reaction mass was concentrated as intact under reduced pressure. Precipitated solid was the desired product. Ethyl 2-cyano-3-hydroxy-4,4,4-trifluoro-2-butenoate sodium salt thus obtained was 221.86 g. The yield was 96 %. Following results were obtained by NMR analysis. 1H-NMR (acetone-d6, bppm): 1.21(3H, t, J=6.9 Hz), 4.09(2H, q, J=6.9 Hz)

Workup

  1. customTo a solution obtained
  2. additionwas dropwise added
  3. stirringAfter stirring for one hour
  4. stirringstirred for 3 hours at the same temperature
  5. customthe reaction
  6. concentrationthe reaction mass was concentrated as intact under reduced pressure
  7. customPrecipitated solid

Sources & evidence

ORD record
ord-36335d32f8c7481ebd563f1003ecc216
Source dataset
uspto-grants-2001_05
Patent number
US06235911B1

Reaction notes

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