Dimethylcarbamoyl Chloride → HCID 22494275, Verbindung

HRID 1816592Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1816592
[CH3:1][N:2](C)C(Cl)=O.C([O-])(=O)CCCCCCC/C=C\CCCCCCCC.[CH2:27]([O:29][C:30](=[O:43])[CH:31]([O:39][CH:40]([CH3:42])[CH3:41])[CH2:32][C:33]1[CH:38]=[CH:37][NH+:36]=[CH:35][CH:34]=1)[CH3:28].C[Si](C#N)(C)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:1]([C:37]1[CH:38]=[C:33]([CH2:32][CH:31]([O:39][CH:40]([CH3:42])[CH3:41])[C:30]([O:29][CH2:27][CH3:28])=[O:43])[CH:34]=[CH:35][N:36]=1)#[N:2]

Komponenten

6

Edukt 4

HCID 6598Dimethylcarbamoyl ChlorideHCID 11430Potassium CarbonateHCID 82115Trimethylsilyl cyanideHCID 69801129HCID 69801129, Verbindung

Produkt 1

HCID 22494275HCID 22494275, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

2.3 mL dimethyl carbamyl chloride was added dropwise over 40 minutes into a solution of 6.40 g crude 4-(3-ethoxy-2-isopropoxy-3-oxopropyl)-1-pyridinium oleate and 3.3 mL trimethylsilyl cyanide in dichloromethane (60 mL), followed by stirring for 11.5 hours. 10% aqueous potassium carbonate was added to the reaction solution, followed by stirring at room temperature for 30 minutes. The organic layer was dried over anhydrous sodium sulfate and concentrated. The residue was purified by silica gel flash column chromatography, to give 3.87 g of ethyl 3-(2-cyano-4-pyridyl)-2-isopropoxypropanoate as a pale yellow oil.

Aufarbeitung

  1. stirringby stirring at room temperature for 30 minutes
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. concentrationconcentrated
  4. customThe residue was purified by silica gel flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-e7fbc273b335441fa0e87c8d899086ff
Quelldatensatz
uspto-grants-2005_04
Patentnummer
US06884821B1

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