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Water → HCID 66971328, Verbindung

HRID 2102323
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2102323
[CH2:1]([O:8][C:9]1[C:13]([CH:14]=[O:15])=[C:12]([CH:16]([CH3:18])[CH3:17])[N:11]([CH:19]([CH3:21])[CH3:20])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]1([Mg]Br)[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+].O>O1CCCC1>[CH2:1]([O:8][C:9]1[C:13]([CH:14]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[OH:15])=[C:12]([CH:16]([CH3:17])[CH3:18])[N:11]([CH:19]([CH3:21])[CH3:20])[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 962WaterHCID 25517Ammonium ChlorideHCID 23079526HCID 23079526, VerbindungHCID 178418255HCID 178418255, Verbindung

Produkt 1

HCID 66971328HCID 66971328, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 3-benzyloxy-4-formyl-1,5-diisopropyl-1H-pyrazole (0.21 g) in tetrahydrofuran (10 mL) was added a solution of phenylmagnesium bromide in tetrahydrofuran (1 mol/L, 1.5 mL) at room temperature, and the mixture was stirred at room temperature for 2 hours. A saturated ammonium chloride aqueous solution and water were added to the reaction mixture, and the mixture was purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran). Further purification by column chromatography on silica gel (eluent:hexane/ethyl acetate=10/1-2/1) to give the adduct material, [3-benzyloxy-1,5-diisopropyl-1H-pyrazole-4-yl] phenyl methanol. The obtained adduct material was dissolved in ethanol, and a catalytic amount of 10% palladium-carbon powder was added to the solution. The mixture was stirred at room temperature under a hydrogen atmosphere overnight. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (0.16 g).

Aufarbeitung

  1. customthe mixture was purified by column chromatography on aminopropylated silica gel (eluent:tetrahydrofuran)
  2. customFurther purification by column chromatography on silica gel (eluent:hexane/ethyl acetate=10/1-2/1)

Quellen und Nachweise

ORD-Eintrag
ord-92fa240cb9f6441b9dde8ad1bd8af469
Quelldatensatz
uspto-grants-2009_08
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07576063B2

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