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

HRID 1351300Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1351300
[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

Komponenten

7

Edukt 2

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

Produkt 1

HCID 860714225-Formylthiophene-3-sulfonic acid [2-(4-fluorophenyl)ethyl]-methyl-amideAusbeute 41,8 %

Reagenzien, Katalysatoren, Lösungsmittel 4

HCID 6093376Ruthenium trichloride hydrateKatalysatorHCID 962WaterLösungsmittelHCID 6344DichloromethaneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-d25aacb732b84048aec7925dc1f06cb3
Quelldatensatz
uspto-grants-2007_05
Patentnummer
US07217723B2

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