Sodium Carbonate → 4-(4-acetylphenyl)-2-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

HRID 2298294Notes

Reaction equation

HRID 2298294 reaction equation
[CH2:1]([C:3]1([CH3:20])[C:7](=[O:8])[C:6](I)=[C:5]([C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)[O:4]1)[CH3:2].C(=O)([O-])[O-].[Na+].[Na+].[C:27]([C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1)(=[O:29])[CH3:28]>C1(C)C=CC=CC=1.C(O)C.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>[C:27]([C:30]1[CH:35]=[CH:34][C:33]([C:6]2[C:7](=[O:8])[C:3]([CH2:1][CH3:2])([CH3:20])[O:4][C:5]=2[C:10]2[CH:15]=[CH:14][C:13]([S:16]([CH3:19])(=[O:18])=[O:17])=[CH:12][CH:11]=2)=[CH:32][CH:31]=1)(=[O:29])[CH3:28]

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 37021224-Acetylphenylboronic acidHCID 183855942-ethyl-4-iodo-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone

Product 1

HCID 183856354-(4-acetylphenyl)-2-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanoneYield 61.2%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 1140TolueneSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of 2-ethyl-4-iodo-2-methy-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone (200 mg) in 15 ml toluene and 5 ml ethanol, were added 34 mg of tetrakis(triphenylphosphine)palladium(0), 5 ml of 2M aqueous sodium carbonate solution and 120 mg of 4-acetylbenzeneboronic acid. Then the reaction solution was stirred at 95° C. for 12 hours. The reaction solvent was evaporated off under reduced pressure and the resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3). Then the organic layer was concentrated in vacuo and the resulting crude product was purified by column chromatography (hexane/ethylacetate) to afford 120 mg of 4-(4-acetylphenyl)-2-ethyl-2-methyl-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone as a solid. mp: 147-148° C. NMR: δ0.97 (t, J=7.5 Hz, 3H), 1.56 (s, 3H), 1.99 (m, 2H), 2.62 (s, 3H), 3.08 (s, 3H), 7.39 (d, J=8.7 Hz, 2H), 7.83 (d, J=8.7 Hz, 2H), 7.97 (m, 2H). IR (cm−1): 2929, 1684, 1410, 1317, 1149, 1016, 769, 552.

Workup

  1. customThe reaction solvent was evaporated off under reduced pressure
  2. extractionthe resulting residue was extracted with 50 ml water and dichloromethane (30 ml×3)
  3. concentrationThen the organic layer was concentrated in vacuo
  4. customthe resulting crude product was purified by column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-0bed4ec96e454b9bbb6ccfe26abe74ab
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

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