Selenium Dioxide → HCID 18669516, compound

HRID 1058990Notes

Reaction equation

HRID 1058990 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH3:16])[O:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1.[Se](=O)=[O:28]>O1CCOCC1>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14](=[O:15])[CH:13]=[C:12]([CH:16]=[O:28])[O:11][C:10]=1[C:17]1[CH:22]=[CH:21][C:20]([S:23]([CH3:26])(=[O:25])=[O:24])=[CH:19][CH:18]=1

Participants

4

Reactant 2

HCID 24007Selenium DioxideHCID 11222615HCID 11222615, compound2×

Product 1

HCID 18669516HCID 18669516, compoundYield 48.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
180 °C

Procedure

To a solution of 3-(2,4-difluorophenyl)-2-(4-methanesulfonylphenyl)-6-methylpyran-4-one (1.7 g; 4.5 mmoles) (compound 13) in dioxane (45 ml), selenium dioxide (2.2 g, 20 mmoles) was added and the mixture heated in a pressure vessel at 180° C. for 1 hour. After cooling, the reaction mixture was filtered, the solvent removed under reduced pressure and the residual oil purified by column chromatography with silica gel and ethyl acetate as eluent. 5-(2,4difluorophenyl)-6-(4-methanesulfonylphenyl)-4-oxo-4H-pyran-2-carbaldehyde (0.85 g) was obtained.

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction mixture was filtered
  3. customthe solvent removed under reduced pressure
  4. customthe residual oil purified by column chromatography with silica gel and ethyl acetate as eluent

Sources & evidence

ORD record
ord-5447d7dd997443be8bf27764f3206796
Source dataset
uspto-grants-2003_02
Patent number
US06518303B2

Reaction notes

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