Sodium hydride → methyl 4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzoate

HRID 507969Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507969
[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[NH:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].[H][H].Br[CH2:19][C:20]1[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=1>CN(C)C=O.O>[C:1]([C:5]1[CH:9]=[C:8]([C:10]([CH3:13])([CH3:12])[CH3:11])[N:7]([CH2:19][C:20]2[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Komponenten

7

Edukt 4

HCID 24758Sodium hydrideHCID 1369123,5-Di-t-butylpyrazoleHCID 256687Methyl 4-(bromomethyl)benzoateHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 23157342methyl 4-[(3,5-di-tert-butyl-1H-pyrazol-1-yl)methyl]benzoateAusbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 3,5-di-tert-butyl-1H-pyrazole (1.00 g, 5.55 mmol) in N,N-dimethylformamide (15 mL) was added sodium hydride (60% in oil, 0.27 g, 6.8 mmol) under ice-cooling. After completion of hydrogen generation, methyl 4-(bromomethyl)benzoate (1.40 g, 6.11 mmol) was added, and the mixture was stirred overnight at room temperature. Water was added to the reaction mixture, and the precipitated solid was collected by filtration, washed with water, and dried to give the title compound (1.78 g, yield 98%) as colorless crystals.

Aufarbeitung

  1. temperaturecooling
  2. filtrationthe precipitated solid was collected by filtration
  3. washwashed with water
  4. customdried

Quellen und Nachweise

ORD-Eintrag
ord-c643fa32768a4893a3589e6b72156472
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786165B2

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