Sodium Carbonate → 4-Ethyl-3-(pyridin-3-yl)benzaldehyde

HRID 460155Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 460155
Br[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[CH2:10][CH3:11])[CH:5]=[O:6].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O.C([O-])(O)=O.[Na+].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>[CH2:10]([C:9]1[CH:8]=[CH:7][C:4]([CH:5]=[O:6])=[CH:3][C:2]=1[C:14]1[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=1)[CH3:11]

Komponenten

8

Edukt 3

HCID 10340Sodium CarbonateHCID 27343783-Pyridinylboronic acidHCID 222596893-Bromo-4-ethylbenzaldehyde

Produkt 1

HCID 223911924-Ethyl-3-(pyridin-3-yl)benzaldehydeAusbeute 49,4 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittelHCID 516892Sodium BicarbonateLösungsmittel

Versuchsvorschrift

To a mixture of 3-bromo-4-ethylbenzaldehyde (2.45 g, 0.0115 mol), pyridine 3-boronic acid (1.42 g, 0.0115 mol, Matrix Scientific), 2M Na2CO3 (15 mL) in 30 mL of toluene was added 1.33 g of Pd (PPh3)4 (1.15 mmol, Aldrich). The mixture was then heated to 80 C under N2 for 16 hours. The mixture was cooled to RT and was diluted with 100 mL of EtOAc and 40 mL of sat. NaHCO3 aq. solution. The organic phase was washed with 40 mL of brine, dried over Na2SO4 and concentrated in vacuo. The crude product was chromatographed (silica gel, 20% EtOAc in hexane) to provide yellow oil (1.2 g).

Aufarbeitung

  1. temperatureThe mixture was then heated to 80 C under N2 for 16 hours
  2. washThe organic phase was washed with 40 mL of brine
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe crude product was chromatographed (silica gel, 20% EtOAc in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-f67c664d59db44f78b38654a881134de
Quelldatensatz
uspto-grants-2007_03
Patentnummer
US07196102B2

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