Sodium hydride → 2,2-dimethyl-4-(3-fluorophenyl)-5-{(methylsulfonyl)phenyl}-3(2H)-furanone

HRID 2298270Notes

Reaction equation

HRID 2298270 reaction equation
[CH3:1][C:2]1([CH3:25])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][C:18](S(C)(=O)=O)=[CH:17][CH:16]=2)[O:3]1.FC1C=C(CC(C2C=C[C:39]([S:42](C)(=[O:44])=[O:43])=CC=2)=O)C=CC=1.[H-].[Na+].BrC(C)(C)C(C#N)=O>C1COCC1>[CH3:1][C:2]1([CH3:25])[C:6](=[O:7])[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([F:14])[CH:9]=2)=[C:4]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[S:42]([CH3:39])(=[O:44])=[O:43])[O:3]1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 99507622,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanoneHCID 112200462-(3-Fluorophenyl)-1-(4-methylsulfonylphenyl)-ethanone2×HCID 124878382-Bromo-2-methylpropanoyl cyanide

Product 1

HCID 183856632,2-dimethyl-4-(3-fluorophenyl)-5-{(methylsulfonyl)phenyl}-3(2H)-furanone

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Another variation to prepare 2,2-dimethyl-4-(3-fluorophenyl)-5-{4-(methylsulfonyl)phenyl}-3(2H)-furanone was performed starting from 2-(3-fluorophenyl)-1-{4-(methylsulfonyl)phenyl}-ethanone as follows: To a stirred solution of 2-(3-fluorophenyl)-1-(4-methylsulfonylphenyl)-ethanone (1 g) in 10 ml of THF, was added 0.23 g of 95% sodium hydride at 0° C. The reaction solution was stirred for 1 hour at the same temperature. Then 0.64 g of a-bromo-isobutyric cyanide was added dropwise to the reaction mixture at 0° C. The reaction mixture was stirred for another 7 hours while being allowed to warm to room temperature. Then the reaction was quenched with 5 ml of water. The mixture was concentrated in vacuo, and was dissolved in 50 ml of water. The aqueous solution was extracted with ethylacetate (100 ml). The organic layer was washed with brine, concentrated in vacuo. Then the resulting residue was purified by column chromatography (hexane/ethylacetate) to afford 0.75 g of 2,2-dimethyl-4-(3-fluorophenyl)-5-{(methylsulfonyl)phenyl}-3(2H)-furanone.

Workup

  1. stirringThe reaction mixture was stirred for another 7 hours
  2. customThen the reaction was quenched with 5 ml of water
  3. concentrationThe mixture was concentrated in vacuo
  4. dissolutionwas dissolved in 50 ml of water
  5. extractionThe aqueous solution was extracted with ethylacetate (100 ml)
  6. washThe organic layer was washed with brine
  7. concentrationconcentrated in vacuo
  8. customThen the resulting residue was purified by column chromatography (hexane/ethylacetate)

Sources & evidence

ORD record
ord-63a8e92a6f604c92b3c78d85b7d0c44c
Source dataset
uspto-grants-2002_12
Patent number
US06492416B1

Reaction notes

Loading…