Sodium Chloride → HCID 68115395, Verbindung

HRID 525059

Reaktionsgleichung

Reaktionsgleichung von HRID 525059
[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]

Komponenten

7

Edukt 4

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

Produkt 1

HCID 68115395HCID 68115395, VerbindungAusbeute 32 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

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)+.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-e765755804404f4fa2800d15355e2ebe
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09340554B2

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