Acetone → 4-[2-Fluoro-4-(methylsulfonyl)phenyl]-3-(4-fluorophenyl)-2(5H)-furanone
Reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=[O:22])[O:10][CH2:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16](SC)=[CH:15][C:14]=2[F:21])=[CH:4][CH:3]=1.O[O:24][S:25]([O-:27])=O.[K+].[CH3:29]C(C)=O>O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9](=[O:22])[O:10][CH2:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([S:25]([CH3:29])(=[O:27])=[O:24])=[CH:15][C:14]=2[F:21])=[CH:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To a solution of 3-(4-fluorophenyl)-4-(2-fluoro-4-methylsulfanylphenyl)-2,5-dihydro-2-furanone (6 g, 18.8 mmol) (obtained in step 2) in acetone (150 ml) was added a solution of oxone (34.8 g, 56.6 mmol) in water (75 ml). The reaction mixture was stirred vigorously for 2 h at 25° C. After completion of the reaction solvent was removed under low vacuum and water (200 ml) was added to it. The mixture was then extracted with EtOAc (2×100 ml), organic layers collected, combined, dried over anhydrous Na2SO4 and concentrated under vacuum. The crude product was then treated with MeOH (2×20 ml) and filtered to give 5.6 g of title compound in 85% yield as off white powder. m.p. 160°-162° C.
Workup
- customAfter completion of the reaction solvent was removed under low vacuum and water (200 ml)
- additionwas added to it
- extractionThe mixture was then extracted with EtOAc (2×100 ml), organic layers
- customcollected
- dry with materialdried over anhydrous Na2SO4
- concentrationconcentrated under vacuum
- additionThe crude product was then treated with MeOH (2×20 ml)
- filtrationfiltered
Sources & evidence
- ORD record
- ord-8a4f6880254842a1ba4287313d2868d3
- Source dataset
- uspto-grants-2004_02
- Patent number
- US06686390B2
Reaction notes
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