Ethanol → HCID 18472376, Verbindung

HRID 565858Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 565858
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+].[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:25]([OH:27])[CH3:26]>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>[CH3:24][C:18]1[CH:23]=[CH:22][C:21]([C:3]2[CH:8]=[C:7]3[C:6]([CH2:9][CH2:26][C:25]3=[O:27])=[CH:5][CH:4]=2)=[CH:20][CH:19]=1

Komponenten

7

Edukt 4

HCID 702EthanolHCID 1140TolueneHCID 11430Potassium CarbonateHCID 866453334-Methylphenyl borate

Produkt 1

HCID 18472376HCID 18472376, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 962WaterLösungsmittel

Versuchsvorschrift

Under argon atmosphere, a mixture of 6-(trifluoromethanesulfoxy)-1-indanone (11. 5 g), 4-methylphenyl borate (6.69 g), potassium carbonate (11.3 g), toluene (400 ml), ethanol (40 ml) and water (40 ml) was stirred at room temperature for 30 minutes, and to the mixture was added tetrakis(triphenylphosphine)palladium (1.42 g). The mixture was refluxed for 17 hours and cooled to room temperature. The organic layer was separated, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/toluene=1/10) and recrystallized from ethyl acetate-hexane to give 6-(4-methylphenyl)-1-indanone (5.20 g) as pale brown crystals.

Aufarbeitung

  1. temperatureThe mixture was refluxed for 17 hours
  2. temperaturecooled to room temperature
  3. customThe organic layer was separated
  4. dry with materialdried with anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was separated
  7. custompurified with column chromatography (ethyl acetate/toluene=1/10)
  8. customrecrystallized from ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-ce999a209bb24b0f8819bf671c137950
Quelldatensatz
uspto-grants-2001_01
Patentnummer
US06172061B2

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