Ethanol → HCID 18472376, compound

HRID 1387791Notes

Reaction equation

HRID 1387791 reaction equation
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

Participants

7

Reactant 4

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

Product 1

HCID 18472376HCID 18472376, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Under argon atmosphere, a mixture of 6-(trifluromethanesulfoxy)-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.

Workup

  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

Sources & evidence

ORD record
ord-e395552a314d445fac7968d041cb8c9a
Source dataset
uspto-grants-2001_07
Patent number
US06268354B1

Reaction notes

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