Water → HCID 59334476, Verbindung

HRID 1639749Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1639749
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[CH3:9][C:10]1[N:25]=[C:13]2[C:14](/[CH:18]=[CH:19]/[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1.O>CS(C)=O>[CH3:9][C:10]1[N:25]=[C:13]2[C:14]([CH:18]3[CH2:4][CH:19]3[C:20]([O:22][CH2:23][CH3:24])=[O:21])=[CH:15][CH:16]=[CH:17][N:12]2[N:11]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 66720782HCID 66720782, Verbindung

Produkt 1

HCID 59334476HCID 59334476, VerbindungAusbeute 43,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 679Dimethyl SulfoxideLösungsmittel3×

Versuchsvorschrift

Under nitrogen atmosphere, to a suspension of sodium hydride (0.830 g, 20.8 mmol) in dimethyl sulfoxide (10 mL) was added a solution of trimethylsulfoxonium iodide (4.57 g, 20.8 mmol) in dimethyl sulfoxide (35 mL) at 0° C., and the mixture was stirred at room temperature for 1 hr. To the reaction mixture was added a solution of ethyl (2E)-3-(2-methyl[1,2,4]triazolo[1,5-a]pyridin-8-yl)acrylate (4.00 g, 17.3 mmol) in dimethyl sulfoxide (30 mL) at 0° C., and the mixture was stirred at room temperature for 14 hr. Water was added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2) to give the title compound (1.84 g, yield 43%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for 14 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane=1/2)

Quellen und Nachweise

ORD-Eintrag
ord-9eba9d23ead248e3ba0f799671668316
Quelldatensatz
uspto-grants-2012_02
Patentnummer
US08110585B2

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