Water → 2-Methyl-7-phenyl-1-indanone

HRID 2298467Notes

Reaction equation

HRID 2298467 reaction equation
Cl[C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[C:9](=[O:11])[CH:8]([CH3:12])[CH2:7]2.[C:13]1(B(O)O)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+].O>C(O)CO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:12][CH:8]1[CH2:7][C:6]2[C:10](=[C:2]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH:3]=[CH:4][CH:5]=2)[C:9]1=[O:11]

Participants

7

Reactant 4

HCID 962Water2×HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 117898227-Chloro-2-methyl-2,3-dihydro-1H-inden-1-one

Product 1

HCID 185126012-Methyl-7-phenyl-1-indanoneYield 68.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 174Ethylene GlycolSolvent

Conditions

Temperature
125 °C

Procedure

0.9 g (5 mmol) of (1), 0.73 g (6 mmol) of phenylboronic acid and 1.32 g (12.5 mmol) of sodium carbonate were placed in 15 ml of ethylene glycol/3 ml of water in the reaction vessel, the mixture was degassed a number of times and saturated with argon. After addition of 33.7 mg (0.15 mmol) of palladium acetate and 0.34 g (0.6 mmol) of (m-NaO3S-phenyl)3phosphine (TMSPP), the reaction mixture was stirred for 5 hours at 125° C. After addition of 20 ml of water, the aqueous phase was extracted 5 times with 30 ml each time of ether, the combined ether phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution and dried over magnesium sulfate. Removal of the solvent gave 0.76 g of (15) as solid.

Workup

  1. customthe mixture was degassed a number of times
  2. extractionthe aqueous phase was extracted 5 times with 30 ml each time of ether
  3. washthe combined ether phases were washed with 40 ml of water and 40 ml of saturated sodium chloride solution
  4. dry with materialdried over magnesium sulfate
  5. customRemoval of the solvent

Sources & evidence

ORD record
ord-28ddc099d5674b5eab76ce4f78f9fb6e
Source dataset
uspto-grants-2002_12
Patent number
US06492539B1

Reaction notes

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