5-Vinylthiophene-3-sulfonic acid[2-(4-fluorophenyl)ethyl]-methyl-amide → 5-Formylthiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amide

HRID 1351300Notes

Reaction equation

HRID 1351300 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:21])[S:11]([C:14]2[CH:18]=[C:17]([CH:19]=C)[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1.I([O-])(=O)(=O)=[O:23].[Na+]>ClCCl.O.C(OCC)(=O)C.O.[Ru](Cl)(Cl)Cl>[F:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]([CH3:21])[S:11]([C:14]2[CH:18]=[C:17]([CH:19]=[O:23])[S:16][CH:15]=2)(=[O:13])=[O:12])=[CH:4][CH:3]=1

Participants

7

Reactant 2

HCID 210986625-Vinylthiophene-3-sulfonic acid[2-(4-fluorophenyl)ethyl]-methyl-amideHCID 23667635Sodium periodate

Product 1

HCID 860714225-Formylthiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amideYield 41.8%

Reagents, catalysts & solvents 4

HCID 6093376Ruthenium trichloride hydrateCatalystHCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-vinylthiophene-3-sulfonic acid[2-(4-fluorophenyl)ethyl]-methyl-amide (328 mg) in dichloromethane (2 mL) was added sodium meta periodate (863 mg) and ruthenium trichloride monohydrate (5 mg) at room temperature. After stirring for 2 hours, this solution was diluted with water and ethyl acetate, and Celite filtration was carried out. The organic layer was separated, after drying with anhydrous sodium sulfate, the residue that was obtained upon removing the solvent by evaporation were purified by silica gel column chromatography (hexane/ethyl acetate) and the title compound (138 mg) was obtained as a yellow oily substance.

Workup

  1. customThe organic layer was separated
  2. dry with materialafter drying with anhydrous sodium sulfate
  3. customthe residue that was obtained
  4. customupon removing the solvent
  5. customby evaporation
  6. customwere purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-d25aacb732b84048aec7925dc1f06cb3
Source dataset
uspto-grants-2007_05
Patent number
US07217723B2

Reaction notes

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