Sodium Carbonate → HCID 70211563, Verbindung

HRID 381835

Reaktionsgleichung

Reaktionsgleichung von HRID 381835
[CH3:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[CH:17]=[CH:16][C:15]([C:18](=[O:25])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:14][CH:13]=1.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[CH:13]=[CH:14][C:15]([C:18](=[O:25])[CH2:19][CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:16][CH:17]=2)=[CH:4][CH:3]=1

Komponenten

7

Edukt 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 838865Methyl 4-(4-bromophenyl)-4-oxobutanoate

Produkt 1

HCID 70211563HCID 70211563, VerbindungAusbeute 69,4 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumKatalysatorHCID 1140TolueneLösungsmittel2×HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

To a stirred mixture of (4-methylphenyl)boronic acid (0.818 g, 0.00602 mol) and 4-(4-bromo-phenyl)-4-oxo-butyric acid, methyl ester (1.3556 g, 0.00500 mol) in toluene (10 mL) was added tetrakis(triphenylphosphine)-palladium(0) (0.173 g, 0.000150 mol) and 2.0 M aqueous sodium carbonate (5.0 mL, 0.010 mol), and the mixture was heated at reflux under nitrogen for 12 hours and allowed to cool. The mixture was diluted with toluene and dichloromethane (10 mL/10 mL), and filtered through a pad of Celite. The Celite was washed with additional toluene and dichloromethane. Filtrate and washings were combined and washed with 2.0 M aqueous sodium carbonate, brine, 3% aqueous ammonium hydroxide, water, and brine. The organics were dried (Na2SO4) and rotary evaporated. The residue was dissolved in chloroform and purified by column chromatography on silica gel (144 g, 230-400 mesh), eluting with hexanes-acetone (6:1, 17×125 mL) to give 0.98 g of 4-(4′-methyl-biphenyl-4-yl)-4-oxo-butyric acid, methyl ester as a white solid; mp 121-122° C.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 12 hours
  3. temperatureto cool
  4. filtrationfiltered through a pad of Celite
  5. washThe Celite was washed with additional toluene and dichloromethane
  6. washwashed with 2.0 M aqueous sodium carbonate, brine, 3% aqueous ammonium hydroxide, water, and brine
  7. dry with materialThe organics were dried (Na2SO4) and rotary evaporated
  8. dissolutionThe residue was dissolved in chloroform
  9. custompurified by column chromatography on silica gel (144 g, 230-400 mesh)
  10. washeluting with hexanes-acetone (6:1, 17×125 mL)

Quellen und Nachweise

ORD-Eintrag
ord-e1ad33f04f7945c9b86aacb99e319450
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06307089B2

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