Methanol → 3-(2-Propyl-pyridin-4-yl)-acrylonitrile

HRID 277020Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 277020
[H-].[Na+].[Cl-].[C:4]([CH2:6][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)#[N:5].[CH2:26]([C:29]1[CH:34]=[C:33]([CH:35]=O)[CH:32]=[CH:31][N:30]=1)[CH2:27][CH3:28].CO>O1CCCC1.CN(C)C=O>[CH2:26]([C:29]1[CH:34]=[C:33]([CH:35]=[CH:6][C:4]#[N:5])[CH:32]=[CH:31][N:30]=1)[CH2:27][CH3:28]

Komponenten

7

Edukt 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 197040(Cyanomethyl)triphenylphosphonium chlorideHCID 226296632-Propyl-4-pyridinecarboxaldehyde

Produkt 1

HCID 700871883-(2-Propyl-pyridin-4-yl)-acrylonitrileAusbeute 46,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8028TetrahydrofuranLösungsmittel2×

Versuchsvorschrift

To a suspension of 1.39 g (0.03 mol) sodiumhydride in 40 ml tetrahydrofurane and 40 ml dimethylformamide were added 10.13 g (0.03 mol) (cyanomethyl)triphenylphosphonium chloride. After sirring for 1 hour at room temperature a solution of 4.48 g (0.03 mol) 2-propyl-4-pyridinecarboxaldehyde in 15 ml tetrahydrofuran were added and stirring was continued for 15 hours. Then 10 ml methanol were added) the solvents were evaporated and the residue chromatographed on aluminiumoxide with dichloromethane to yield 2.42 g 3-(2-propyl-pyridin-4-yl)-acrylonitrile as yellow oil. MS m/e (%): 173 (M+H+, 100).

Aufarbeitung

  1. waitwas continued for 15 hours
  2. customwere evaporated
  3. customthe residue chromatographed on aluminiumoxide with dichloromethane

Quellen und Nachweise

ORD-Eintrag
ord-eb89275c9cdb42e8abfba864d3e39d48
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355653B1

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