Potassium Carbonate → HCID 18472441, Verbindung

HRID 1277193Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1277193
[CH3:1][N:2]([O:11][CH3:12])[C:3]([C:5]1[O:6][C:7](Br)=[CH:8][CH:9]=1)=[O:4].B([O-])([O-])O[C:15]1[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1(C)C(CCO)=CC=CC=1.O.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>[CH3:1][N:2]([O:11][CH3:12])[C:3]([C:5]1[O:6][C:7]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)=[CH:8][CH:9]=1)=[O:4]

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 18472462HCID 18472462, VerbindungHCID 866453334-Methylphenyl borate

Produkt 1

HCID 18472441HCID 18472441, VerbindungAusbeute 91,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 66602552Toluene-ethanol waterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a solution of N-methyl-N-methoxy-5-bromofuran-2-carboxamide (2.77 g), 4-methylphenyl borate (1.93 g) and potassium carbonate (3.27 g) in toluene-ethanol-water (110-11-11 ml) was stirred at room temperature for 1 hour. To the reaction mixture was added tetrakistriphenylphosphinepalladium (0.41 g), and the mixture was refluxed for 20 hours and cooled to room temperature. The organic layer was washed with saturated sodium chloride solution, dried with magnesium sulfate and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1:5→1:2→1:1) to give N-methyl-N-methoxy-5-(4-methylphenyl)furan-2-carboxamide (2.65 g) as colorless crystals.

Aufarbeitung

  1. temperaturethe mixture was refluxed for 20 hours
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1:5→1:2→1:1)

Quellen und Nachweise

ORD-Eintrag
ord-48d5a938daa24c9dbe4d891c12123f42
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166006

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