Sodium Carbonate → 2-Ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-4-phenyl-3(2h)-furanone

HRID 2298291Notes

Reaction equation

HRID 2298291 reaction equation
Br[C:2]1[C:3](=[O:20])[C:4]([CH2:18][CH3:19])([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+].[C:27]1(B(O)O)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C1(C)C=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>[CH2:18]([C:4]1([CH3:17])[C:3](=[O:20])[C:2]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=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)[CH3:19]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 66827Phenylboronic AcidHCID 700020604-bromo-2-ethyl-2-methy-5-{4-(methylsulfonyl)-phenyl}-3(2H)-furanone

Product 1

HCID 111641382-Ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-4-phenyl-3(2h)-furanoneYield 30.2%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Procedure

To a stirred solution of 4-bromo-2-ethyl-2-methy-5-{4-(methysulfonyl)-phenyl}-3(2H)-furanone (200 mg) in 15 ml of toluene, were added 40 mg of tetrakis(triphenylphosphine)palladium(0), 5 ml of 2 M aqueous sodium carbonate solution, and 100 mg of benzeneboronic acid. The reaction solution was stirred at reflux for 12 hours. Then the reaction solvent was evaporated under reduced pressure. The resulting residue was extracted with water and dichloromethane (30 ml×3). The organic layer was concentrated in vacuo. The resulting crude product mixture was purified by column chromatography (hexane/ethylacetate=2:1) to give 60 mg of 2-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-4-phenyl-3(2H)-furanone as a solid. mp: 115-117° C. NMR: δ0.96 (t, J=7.5 Hz, 3H), 1.55 (s, 3H), 1.97 (q, J=7.5 Hz, 2H), 3.07 (s, 3H), 7.37 (m, 5H), 7.85 (d, J=8.7 Hz, 2H), 7.93 (d, J=8.7 Hz, 2H). IR (cm−1): 2928, 1697, 1620, 1403, 1318, 1149, 959, 769, 552.

Workup

  1. temperatureat reflux for 12 hours
  2. customThen the reaction solvent was evaporated under reduced pressure
  3. extractionThe resulting residue was extracted with water and dichloromethane (30 ml×3)
  4. concentrationThe organic layer was concentrated in vacuo
  5. customThe resulting crude product mixture was purified by column chromatography (hexane/ethylacetate=2:1)

Sources & evidence

ORD record
ord-ecdddbcf9540449197e2404207c78142
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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