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Water → 5-(4-Chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazole

HRID 9883
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Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 9883
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]2[NH:14][N:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:6][CH:5]=1.[CH3:21][Si:22]([CH3:29])([CH3:28])[CH2:23][CH2:24][O:25][CH2:26]Cl.O>O1CCCC1>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2[N:14]([CH2:26][O:25][CH2:24][CH2:23][Si:22]([CH3:29])([CH3:28])[CH3:21])[N:13]=[CH:12][C:11]=2[C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)=[CH:8][CH:9]=1
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Komponenten

6

Edukt 4

HCID 962WaterHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 219885015-(4-Chlorophenyl)-4-(pyridin-4-yl)pyrazole

Produkt 1

HCID 219884875-(4-Chlorophenyl)-4-(pyridin-4-yl)-1-(2-trimethylsilylethoxy)methylpyrazoleAusbeute 90 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

55% Sodium hydride (1.41 g, 32.1 mmol) was suspended in tetrahydrofuran (300 ml). To the suspension was added 5-(4-chlorophenyl)-4-(pyridin-4-yl)pyrazole (8.21 g, 32.1 mmol), and the resulting mixture was stirred at room temperature for 1 hour. To the resulting mixture was added (2-trimethylsilylethoxy)methyl chloride (5.68 ml, 32.1 mmol) dropwise under ice cooling, and the mixture was stirred at room temperature overnight. At the end of this time, water was added to the mixture and the mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous sodium sulfate and the solvent was removed by distillation under reduced pressure. The residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=3:1), to give the title compound (11.12 g) as a pale brown oil (yield 90%).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature overnight
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was removed by distillation under reduced pressure
  6. customThe residue was purified by column chromatography through silica gel (eluent, hexane:ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-03390b047e824451a249e4a8748421c9
Quelldatensatz
uspto-grants-2006_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07091352B2

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