StartseiteMCPWorkbenchSkills
StartseiteWorkbenchBenachrichtigungenMein Bereich
llms.txt · MCP-AnleitungDatenschutz · Nutzungsbedingungen · Supportv1.8.0
  1. Startseite
  2. /Reaktion

Dimethylformamide → HCID 178500163, Verbindung

HRID 2389129
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2389129
C(=O)([O-])[O-].[K+].[K+].CN(C)C=O.[C:12]([CH:16]1[CH2:21][CH2:20][CH:19]([O:22][C:23]2[CH:32]=[CH:31][C:30]3[C:25](=[CH:26][CH:27]=[C:28]([CH:33]([N+:35]([O-:37])=[O:36])[CH3:34])[CH:29]=3)[CH:24]=2)[CH2:18][CH2:17]1)([CH3:15])([CH3:14])[CH3:13].[C:38]([O:42][CH3:43])(=[O:41])[CH:39]=[CH2:40].[Cl-].[NH4+]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C(OC(=O)C)C.O>[C:12]([C@H:16]1[CH2:21][CH2:20][C@H:19]([O:22][C:23]2[CH:24]=[C:25]3[C:30](=[CH:31][CH:32]=2)[CH:29]=[C:28]([C:33]([N+:35]([O-:37])=[O:36])([CH3:34])[CH2:40][CH2:39][C:38]([O:42][CH3:43])=[O:41])[CH:27]=[CH:26]3)[CH2:18][CH2:17]1)([CH3:13])([CH3:14])[CH3:15]
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

9

Edukt 5

HCID 6228DimethylformamideHCID 7294Methyl AcrylateHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 866429012-(trans-4-Tert-butylcyclohexyloxy)-6-(1-nitroethyl)naphthalene

Produkt 1

HCID 178500163HCID 178500163, Verbindung
Ausbeute 72 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 94433Tetrabutylammonium hydrogen sulfateKatalysatorHCID 962WaterLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
20 °C

Versuchsvorschrift

To a mixture of potassium carbonate (0.1783 g, 1.290 mmol), tetrabutylammonium hydrogen sulfate (0.005110 g, 0.01505 mmol) and N,N-dimethylformamide (3.00 mL, 38.7 mmol) was added 2-(4-tert-butyl-cyclohexyloxy)-6-(1-nitro-ethyl)-naphthalene (0.3821 g, 1.075 mmol). The mixture was stirred for 15 minutes, then methyl acrylate (0.1162 mL, 1.290 mmol) was added while maintaining the temperature at 20° C. (cool water bath). The mixture was stirred and allowed to reach room temperature. Stirring was continued (in slightly below room temperature water bath) for 2 hours and the reaction was monitored by HPLC. Ethylacetate and saturated aq. ammonium chloride were added and the layers were separated. The combined organic layer was dried over MgSO4, filtered, concentrated and purified by flash chromatography (0-20% EtOAc in hexanes) to give the title compound in 72% yield.

Aufarbeitung

  1. stirringThe mixture was stirred
  2. customto reach room temperature
  3. stirringStirring
  4. customin slightly below room temperature
  5. customfor 2 hours
  6. customthe layers were separated
  7. dry with materialThe combined organic layer was dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. custompurified by flash chromatography (0-20% EtOAc in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-07c542c2d8df4d96a20073ec3039eb56
Quelldatensatz
uspto-grants-2012_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08269043B2

Notizen zur Reaktion

Wird geladen…

Auf dieser SeiteKomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion