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

HRID 1058931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1058931
[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-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%).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-ffe2686317ad41d59a8810bf7084cbb8
Quelldatensatz
uspto-grants-2003_02
Patentnummer
US06518289B1

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