Acetic Acid → (trans)Cyan-(3,4-dimethyl-cyclopentylidene)-acetic acid ethyl ester

HRID 1058931Notes

Reaction equation

HRID 1058931 reaction equation
[CH3:1][C@H:2]1[C@H:6]([CH3:7])[CH2:5][C:4](=O)[CH2:3]1.[C:9]([CH2:11][C:12]([O:14][CH2:15][CH3:16])=[O:13])#[N:10].C([O-])(=O)C.[NH4+].C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:15]([O:14][C:12](=[O:13])[C:11]([C:9]#[N:10])=[C:4]1[CH2:3][C@@H:2]([CH3:1])[C@H:6]([CH3:7])[CH2:5]1)[CH3:16]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 7764Ethyl cyanoacetateHCID 517165Ammonium AcetateHCID 643073rel-(3R,4R)-3,4-Dimethylcyclopentanone

Product 1

HCID 12970148(trans)Cyan-(3,4-dimethyl-cyclopentylidene)-acetic acid ethyl esterYield 93%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Trans-3,4-dimethyl cyclopentanone (2.91 g, 25.94 mmol), ethyl cyanoacetate (2.93 g, 25.93 mmol), ammonium acetate (0.20 g, 2.60 mmol), and acetic acid (0.31 g, 5.17 mmol) were heated together in refluxing toluene under a Dean-Starck trap for 24 hours. After cooling and filtration through kieselguhr, evaporation gave the required product as an off-white solid (5.0 g, 93%).

Workup

  1. temperatureAfter cooling
  2. filtrationfiltration
  3. customthrough kieselguhr, evaporation

Sources & evidence

ORD record
ord-ffe2686317ad41d59a8810bf7084cbb8
Source dataset
uspto-grants-2003_02
Patent number
US06518289B1

Reaction notes

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