Potassium Carbonate → 5-Methoxy-3-phenyl-1H-inden-1-one

HRID 331388Notes

Reaction equation

HRID 331388 reaction equation
Br[C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[C:10](=[O:19])/[CH:11]=[CH:12]/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O.Cl[Pd]Cl>[CH3:9][O:8][C:6]1[CH:7]=[C:2]2[C:3](=[CH:4][CH:5]=1)[C:10](=[O:19])[CH:11]=[C:12]2[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 11776TriphenylphosphineHCID 70310518HCID 70310518, compound

Product 1

HCID 703155925-Methoxy-3-phenyl-1H-inden-1-oneYield 63%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of (E)-1-(2-bromo-4-methoxyphenyl)-3-phenyl-2-propen-1-one (6.0 g, 18.91 mmol) obtained in Step 2 in DMF (15 mL) was added PPh3 (1.46 g, 5.68 mmol, 0.3 eq), K2CO3 (5.23 g, 37.83 mmol, 2 eq), and PdCl2 (335 mg, 1.89 mmol, 0.1 eq). The reaction vial was heated to 110° C. for 3 h. After cooling to room temperature, the reaction mixture was diluted with EtOAc and filtered through a Celite pad. The solution was washed with H2O and brine, dried over MgSO4, and concentrated in vacuo. The residue was purified by silica gel column chromatography (EtOAc/hexanes=1:5) to afford the desired product (2.8 g, 63%).

Workup

  1. customThe reaction
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltered through a Celite pad
  4. washThe solution was washed with H2O and brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography (EtOAc/hexanes=1:5)

Sources & evidence

ORD record
ord-a0299e06c2004f64b8275a606b3276f7
Source dataset
uspto-grants-2014_11
Patent number
US08877747B2

Reaction notes

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