Sodium Carbonate → 2,2-dimethyl-5-(4-(methylsulfonyl)phenyl)-4-p-tolylfuran-3(2H)-one

HRID 2298265Notes

Reaction equation

HRID 2298265 reaction equation
Br[C:2]1[C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[O:5][C:6]=1[C:7]1[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=1.C(=O)([O-])[O-].[Na+].[Na+].[CH3:26][C:27]1[CH:32]=[CH:31][C:30](B(O)O)=[CH:29][CH:28]=1>C1C=CC=CC=1.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.C1([Pd-3](C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][C:4]1([CH3:18])[C:3](=[O:19])[C:2]([C:30]2[CH:31]=[CH:32][C:27]([CH3:26])=[CH:28][CH:29]=2)=[C:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13]([CH3:16])(=[O:15])=[O:14])=[CH:9][CH:8]=2)[O:5]1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 79799Tolylboronic acidHCID 183857274-Bromo-2,2-dimethyl-5-[4-(methylsulfonyl)phenyl]-3(2h)-furanone

Product 1

HCID 183857372,2-dimethyl-5-(4-(methylsulfonyl)phenyl)-4-p-tolylfuran-3(2H)-oneYield 66.9%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 178420549HCID 178420549, compoundCatalystHCID 241BenzeneSolvent

Procedure

To a stirred solution of 4-bromo-2,2-dimethyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (110 mg) and tetrakis(triphenylpalladium(0) (54 mg) in 30 ml benzene, were added 2 M aqueous sodium carbonate (0.22 ml) and 4-methyl-benzeneboronic acid (60 mg). The reaction solution was stirred at reflux for 24 hours. Then the solvent was evaporated off under reduced pressure. The resulting residue was extracted with 50 ml water and dichloromethane (50 ml×3). The organic layer was concentrated in vacuo and the resulting residue was separated by column chromatography (hexane/ethylacetate=2:1) to give 76 mg of 2,2-dimethyl-4-(4-methylphenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. mp: 167-168° C. NMR: δ1.57 (s, 6H), 2.38 (s, 3H), 3.07 (s, 3H), 7.17 (m, 4H), 7.89 (m, 4H). IR (cm−1): 1707, 1660, 1531, 1289, 1230. MS (EI): 356 (m).

Workup

  1. temperatureat reflux for 24 hours
  2. customThen the solvent was evaporated off under reduced pressure
  3. extractionThe resulting residue was extracted with 50 ml water and dichloromethane (50 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customthe resulting residue was separated by column chromatography (hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-ed5d0f6d2149453abc2e45f05bd1a4fb
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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