Acrylonitrile → HCID 68292301, Verbindung

HRID 1504963Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1504963
[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([CH:10]([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])=[N:8][CH:9]=1)([O-:3])=[O:2].[C:19](#[N:22])[CH:20]=[CH2:21].CO[Na]>CO>[C:19]([CH2:20][CH2:21][C:10]([C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:9][N:8]=1)([C:15]([O:17][CH3:18])=[O:16])[C:11]([O:13][CH3:14])=[O:12])#[N:22]

Komponenten

5

Edukt 3

HCID 7855AcrylonitrileHCID 2764544HCID 2764544, VerbindungHCID 178418582HCID 178418582, Verbindung

Produkt 1

HCID 68292301HCID 68292301, VerbindungAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a solution of compound 75 (10.5 g, 41 mmol) and acrylonitrile (17.4 g, 328 mmol) in absolute CH3OH (100 mL) was added a catalytic amount of CH3ONa (216 mg, 4 mmol) at room temperature with stirring under N2. The mixture was stirred at room temperature for 10 h under N2. The mixture was diluted with aqNaHCO3 and extracted with DCM. The combined organic layers were washed with brine, dried over Na2SO4, concentrated and purified with silica gel column chromatography (PE:EtOAc=5:1) to give compound 76 (3.3 g, 20%) as a light yellow oil.

Aufarbeitung

  1. stirringThe mixture was stirred at room temperature for 10 h under N2
  2. additionThe mixture was diluted with aqNaHCO3
  3. extractionextracted with DCM
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. custompurified with silica gel column chromatography (PE:EtOAc=5:1)

Quellen und Nachweise

ORD-Eintrag
ord-af0707846eda4e4b8a1cc0f479cbdd6d
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09216957B2

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