1-Bromodecane → Methyl 1-decylpyrazole-4-carboxylate

HRID 1977272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1977272
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[CH:3]=[N:2]1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26].C(OCC)(=O)C>CN(C)C=O>[CH2:17]([N:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[CH:3]=[N:2]1)[CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26]

Komponenten

6

Edukt 4

HCID 81731-BromodecaneHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 9793760Methyl 1H-pyrazole-4-carboxylate

Produkt 1

HCID 21997475Methyl 1-decylpyrazole-4-carboxylateAusbeute 91,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A solution of methyl pyrazole-4-carboxylate (10 g) in N,N-dimethylformamide (100 ml) was treated with potassium carbonate (10.95 g) and 1-bromodecane (19.31 g) and the mixture was stirred for 16 hours at room temperature. Ethyl acetate was added and the solution was washed with water (6x), dried over magnesium sulfate and the evaporated residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution) to give methyl 1-decylpyrazole-4-carboxylate (19.4 g) as a white solid.

Aufarbeitung

  1. washthe solution was washed with water (6x)
  2. dry with materialdried over magnesium sulfate
  3. customthe evaporated residue was purified by silica gel chromatography (5:1 hexane-ethyl acetate elution)

Quellen und Nachweise

ORD-Eintrag
ord-f0658be6345648c9a1efd316d7a6c00f
Quelldatensatz
uspto-grants-2001_05
Patentnummer
US06232290B1

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