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

HRID 1167894Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1167894
[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]

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel

Versuchsvorschrift

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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-3de6020271e44f25b4252e6bf1fad291
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06620829B2

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