Imidazole → HCID 68957642, Verbindung

HRID 2378069Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2378069
N1C=CN=C1.[CH3:6][O:7][C:8]([C:10]1([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([OH:24])=[CH:20][CH:19]=3)[C:14]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:12][CH2:11]1)=[O:9].[Si:31](Cl)([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32]>C1COCC1.[Cl-].[Na+].O>[CH3:6][O:7][C:8]([C:10]1([C:13]2[O:17][N:16]=[C:15]([C:18]3[CH:23]=[CH:22][C:21]([O:24][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])=[CH:20][CH:19]=3)[C:14]=2[C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:11][CH2:12]1)=[O:9]

Komponenten

6

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 136395593HCID 136395593, Verbindung

Produkt 1

HCID 68957642HCID 68957642, VerbindungAusbeute 99,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 57417360Sodium chloride; waterLösungsmittel

Versuchsvorschrift

Imidazole (2.1 g) is added to a solution consisting of the 1-[3-(4-hydroxy-phenyl)-4-phenyl-isoxazol-5-yl]-cyclopropanecarboxylic acid methyl ester (9.6 g) and tert-butyldimethylsilyl chloride (4.7 g) in THF (100 mL). The reaction mixture is stirred at room temperature overnight. Brine solution is added and the reaction mixture is twice extracted with ethyl acetate. The combined extracts are dried and concentrated. Repeated concentration from hexane and then pentane gave 1-{3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-4-phenyl-isoxazol-5-yl}-cyclopropanecarboxylic acid methyl ester (12.8 g.)

Aufarbeitung

  1. extractionthe reaction mixture is twice extracted with ethyl acetate
  2. customThe combined extracts are dried
  3. concentrationconcentrated
  4. concentrationconcentration from hexane

Quellen und Nachweise

ORD-Eintrag
ord-c8685dd35471478789b8de2d53cd3581
Quelldatensatz
uspto-grants-2008_12
Patentnummer
US07470715B2

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