Ethanol → HCID 10633568, compound

HRID 1277027Notes

Reaction equation

HRID 1277027 reaction equation
B([O-])([O-])O[C:3]1[CH:8]=[CH:7][C:6]([CH3:9])=[CH:5][CH:4]=1.[C:12](=[O:15])([O-])[O-].[K+].[K+].[C:18]1([CH3:24])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[CH2:25](O)[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][CH2:25][CH2:26][C:12]3=[O:15])=[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 10633568HCID 10633568, compound

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolvent

Procedure

Under argon atmosphere, a mixture of 7-(trifluoromethanesulfoxy)-1-tetralone (9.02 g), 4-methylphenyl borate (5.00 g), potassium carbonate (8.46 g), toluene (300 ml), ethanol (30 ml) and water (30 ml) was stirred at room temperature for 30 minutes, and to the mixture was added tetrakis(triphenylphosphine)palladium (1.06 g). The mixture was refluxed for 14 hours. The reaction mixture was 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) to give 7-(4-methylphenyl)-1-tetralone (5.23 g) as colorless crystals.

Workup

  1. temperatureThe mixture was refluxed for 14 hours
  2. temperatureThe reaction mixture was cooled 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)

Sources & evidence

ORD record
ord-f0be373e6b9d49bba816ce214b8f7bb3
Source dataset
uspto-grants-2000_12
Patent number
US06166006

Reaction notes

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