Hydrochloric Acid → methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate

HRID 2221610Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2221610
[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CI.[C:25](=O)([O-])[O-].[K+].[K+].Cl>CN(C)C=O>[CH2:1]([O:8][C:9]1[CH:13]=[C:12]([C:14]([O:16][CH3:25])=[O:15])[N:11]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 22930700HCID 22930700, Verbindung

Produkt 1

HCID 22930789methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylic acid (33.00 g), methyl iodide (8.5 mL), potassium carbonate (18.88 g) and N,N-dimethylformamide (300 mL) was stirred overnight at room temperature. The reaction mixture was poured into dilute hydrochloric acid, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried over anhydrous magnesium sulfate and concentrated. The residue was subjected to silica gel column chromatography to give methyl 3-benzyloxy-1-phenyl-1H-pyrazole-5-carboxylate (33.48 g, yield 97%) as colorless crystals from a fraction eluted with ethyl acetate-hexane (1:4, v/v). The crystals were recrystallized from ethyl acetate-hexane. melting point: 53-54° C.

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-19fdea61cd454ca59d9a64da73c878b4
Quelldatensatz
uspto-grants-2008_05
Patentnummer
US07368578B2

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