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

HRID 458012Notes

Reaction equation

HRID 458012 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-Stark 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-a0a01d2ca7904c7eab86048a93e4722d
Source dataset
uspto-grants-2007_03
Patent number
US07189747B2

Reaction notes

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