Ethanol → 4-(Pyridin-3-yl)benzaldehyde

HRID 1784661Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1784661
[CH:1]([C:3]1[CH:8]=[CH:7][C:6](OB(O)O)=[CH:5][CH:4]=1)=[O:2].C(=O)([O-])[O-].[Na+].[Na+].C(O)C.Br[C:23]1[CH:24]=[N:25][CH:26]=[CH:27][CH:28]=1>C1(C)C=CC=CC=1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.O>[N:25]1[CH:26]=[CH:27][CH:28]=[C:23]([C:6]2[CH:7]=[CH:8][C:3]([CH:1]=[O:2])=[CH:4][CH:5]=2)[CH:24]=1

Komponenten

8

Edukt 4

HCID 702EthanolHCID 10340Sodium CarbonateHCID 122863-BromopyridineHCID 21940015p-Formylphenylboric acid

Produkt 1

HCID 36930464-(Pyridin-3-yl)benzaldehydeAusbeute 25,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium (0.65 g, 0.56 mmol), 4-formylphenylboric acid (2.81 g, 18.7 mmol), 2M aqueous sodium carbonate (18.7 ml, 37.4 mmol) and ethanol were added to the nitrogen-saturated solution of 3-bromopyridine (2.66 g, 16.8 mmol) in toluene and refluxed under nitrogen for 8 hrs. Water was added to the solution and extracted with ethyl acetate, washed with water and brine and dried. Solvents were removed under reduced pressure and the residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1.5) to give 4-(3-pyridyl)benzaldehyde (0.78 g, 25%).

Aufarbeitung

  1. temperaturerefluxed under nitrogen for 8 hrs
  2. extractionextracted with ethyl acetate
  3. washwashed with water and brine
  4. customdried
  5. customSolvents were removed under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (eluent; hexane/ethyl acetate=1/1.5)

Quellen und Nachweise

ORD-Eintrag
ord-f69f463b37f64448b84e3814c8772d08
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07504411B2

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