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Triacetoxyperiodinane → 1-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamide

HRID 238960
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 238960
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH2:14][OH:15])=[CH:11][C:10]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[O:17])=[C:9]2[CH3:29])=[C:4]([C:30]([F:33])([F:32])[F:31])[CH:3]=1.CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O>ClCCl.C(OCC)(=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[C:12]([CH2:13][CH:14]=[O:15])=[CH:11][C:10]([C:16]([NH:18][C:19]3[CH:24]=[CH:23][C:22]([S:25]([CH3:28])(=[O:27])=[O:26])=[CH:21][CH:20]=3)=[O:17])=[C:9]2[CH3:29])=[C:4]([C:30]([F:31])([F:33])[F:32])[CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 159087TriacetoxyperiodinaneHCID 452787801-[4-Chloro-2-(trifluoromethyl)phenyl]-5-(2-hydroxyethyl)-2-methyl-N-[4-(methylsulfonyl)phenyl]-1H-pyrrole-3-carboxamide

Produkt 1

HCID 866586531-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamideAusbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344Dichloromethane
Lösungsmittel
HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

To a solution of the compound (1.0 g, 2.0 mmol) of Example 1 in dichloromethane (10 mL), Dess-Martin reagent (1.3 g, 3.0 mmol) was added at 0° C. The reaction temperature was raised to room temperature, and after the mixture was further stirred for 1 hour, it was diluted with ethyl acetate and the organic layer was washed with an aqueous sodium hydrogencarbonate solution, an aqueous sodium thiosulfate solution, water and saturated brine. After the solution was dried with sodium sulfate, it was filtered and the solvent was distilled off under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1) to give 1-[4-chloro-2-(trifluoromethyl)phenyl]-2-methyl-N-[4-(methylsulfonyl)phenyl]-5-(2-oxoethyl)-1H-pyrrole-3-carboxamide (0.85 g, 85%).

Aufarbeitung

  1. washthe organic layer was washed with an aqueous sodium hydrogencarbonate solution
  2. dry with materialAfter the solution was dried with sodium sulfate, it
  3. filtrationwas filtered
  4. distillationthe solvent was distilled off under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=1:1)

Quellen und Nachweise

ORD-Eintrag
ord-0f6f24331b0345dbb224094bc25a3849
Quelldatensatz
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08642640B2

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