Water → 4-Methoxy-3-(pyridin-3-yl)benzaldehyde

HRID 1860811

Reaktionsgleichung

Reaktionsgleichung von HRID 1860811
[C:1](=[O:4])([O-])[O-].[Na+].[Na+].[CH:7]([OH:11])(O)[CH2:8][CH3:9].[N:12]1[CH:17]=[CH:16][CH:15]=[C:14](B(O)O)[CH:13]=1.O>C1(C)C=CC=CC=1.C(O)C.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>[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:14]2[CH:13]=[C:8]([CH:9]=[CH:16][C:15]=2[O:4][CH3:1])[CH:7]=[O:11])[CH:13]=1

Komponenten

7

Edukt 3

HCID 962WaterHCID 10340Sodium CarbonateHCID 69587225Pyridine-3-boronic acid propane diol

Produkt 1

HCID 223915214-Methoxy-3-(pyridin-3-yl)benzaldehydeAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 702EthanolLösungsmittelHCID 1140TolueneLösungsmittel

Versuchsvorschrift

Tetrakis(triphenylphosphine)palladium(0) (0.2 g) was added to a solution of 3-bromo-4-methoxybenzldehyde (1.25 g) in toluene (10 ml) and ethanol (10 ml), followed by addition of 2M aqueous sodium carbonate (11 ml). To this mixture was added pyridine-3-boronic acid propane diol (1 g), and the mixture was heated to reflux. After 2 hours, the reaction was added to water (75 ml) and extracted with ethyl acetate (2×75 ml). The combined organic layers were washed with saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml), dried over magnesium sulfate and concentrated. Chromatography (silica, 20-50% ethyl acetate/hexanes) afforded 1.08 g (87%) of 3-(3-pyridyl)-4-methoxybenzaldehyde as a white solid.

Aufarbeitung

  1. temperaturethe mixture was heated to reflux
  2. extractionextracted with ethyl acetate (2×75 ml)
  3. washThe combined organic layers were washed with saturated aqueous sodium bicarbonate (100 ml) and brine (100 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-877ab030e4aa47968e538d56a677f0f1
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531502B1

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