Sodium Chloride → (E)-ethyl 2-cyano-2-(2,2-dimethylcyclopentylidene)acetate

HRID 2369389Notes

Reaction equation

HRID 2369389 reaction equation
[CH3:1][C:2]1([CH3:8])[CH2:6][CH2:5][CH2:4][C:3]1=O.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].C([O-])(=O)C.[NH4+].[Na+].[Cl-]>C1(C)C=CC=CC=1.C(O)(=O)C>[C:9](/[C:11](=[C:3]1\[C:2]([CH3:8])([CH3:1])[CH2:6][CH2:5][CH2:4]\1)/[C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10]

Participants

7

Reactant 4

HCID 5234Sodium ChlorideHCID 7764Ethyl cyanoacetateHCID 1382862,2-DimethylcyclopentanoneHCID 517165Ammonium Acetate

Product 1

HCID 68115395(E)-ethyl 2-cyano-2-(2,2-dimethylcyclopentylidene)acetateYield 32%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 1140TolueneSolvent

Procedure

2,2-dimethylcyclopentanone (5 g, 44.6 mmol, 1 equiv.) was dissolved in toluene (100 mL). Then, ethyl 2-cyanoacetate (5.04 g, 44.6 mmol, 1 equiv.), ammonium acetate (2.4 g, 31.2 mmol, 0.7 equiv.) and acetic acid (2.8 mL) were added in the mixture at room temperature. The mixture was refluxed for 20 hours. 10% NaCl solution (100 mL) was added in the mixture. Then, the organic layer was washed by water (50 mL) and brine (50 mL), dried by sodium sulfate and filtered. The organic layer was concentrated and the residue was purified by column chromatography to give (E)-ethyl 2-cyano-2-(2,2-dimethylcyclopentylidene)acetate (2.47 g, 32%) as a colorless oil. MS: m/z 208 (M+H)+.

Workup

  1. temperatureThe mixture was refluxed for 20 hours
  2. washThen, the organic layer was washed by water (50 mL) and brine (50 mL)
  3. dry with materialdried by sodium sulfate
  4. filtrationfiltered
  5. concentrationThe organic layer was concentrated
  6. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b8dd008dd0514423bd422bc4cad78408
Source dataset
uspto-grants-2014_04
Patent number
US08703941B2

Reaction notes

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