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Acetone → ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate

HRID 1293572
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1293572
[I-].[Na+].[C:3](=[O:6])([O-])[O-].[K+].[K+].Cl[C:10]([O:12][CH:13]([CH3:15])[CH3:14])=[O:11].[CH:16]([O:19][C:20]1[C:21]([O:41][CH3:42])=[CH:22][C:23]([N+:38]([O-:40])=[O:39])=[C:24]([CH:37]=1)[C:25]([C:27]1[NH:31][N:30]=[N:29][C:28]=1[C:32]([O:34][CH2:35][CH3:36])=[O:33])=[O:26])([CH3:18])[CH3:17].[CH3:43][C:44]([CH3:46])=O>O>[CH:13]([O:12][C:10]([O:6][CH:3]([N:30]1[N:29]=[C:28]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:27]([C:25](=[O:26])[C:24]2[CH:37]=[C:20]([O:19][CH:16]([CH3:18])[CH3:17])[C:21]([O:41][CH3:42])=[CH:22][C:23]=2[N+:38]([O-:40])=[O:39])=[N:31]1)[CH:44]([CH3:46])[CH3:43])=[O:11])([CH3:15])[CH3:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 5

HCID 180AcetoneHCID 5238Sodium IodideHCID 7917Isopropyl chloroformateHCID 11430Potassium CarbonateHCID 178470513HCID 178470513, Verbindung

Produkt 1

HCID 22222605
ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate
Ausbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

Isobutyl aldehyde (2.9 ml), sodium iodide (3.18 g), potassium carbonate (11.69 g), and isopropyl chloroformate (7.2 ml) were added in that order under an argon atmosphere at room temperature to a solution of ethyl 5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-1H-1,2,3-triazole-4-carboxylate (8.01 g), prepared in step (32a), in acetone (150 ml). The mixture was stirred at that temperature for 19.5 hr. Water was added to the reaction mixture to stop the reaction. The mixture was extracted with ethyl acetate. The organic layer was washed with 20% saline and dried over anhydrous magnesium sulfate. The solvent was evaporated. The resultant mixture was purified by column chromatography on silica gel (hexane/ethyl acetate) to give ethyl 2-(1-isopropoxycarbonyloxy-2-methylpropyl)-5-(5-isopropoxy-4-methoxy-2-nitrobenzoyl)-2H-1,2,3-triazole-4-carboxylate (10.12 g, 89%).

Aufarbeitung

  1. customthe reaction
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with 20% saline
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated
  6. customThe resultant mixture was purified by column chromatography on silica gel (hexane/ethyl acetate)

Quellen und Nachweise

ORD-Eintrag
ord-26728def83a2463db51c6757d920201d
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07238812B2

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