Water → ethyl 3-(1-benzyl-3-ethoxy-1H-pyrazol-4-yl)propionate

HRID 349941Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 349941
[H-].[Na+].[CH2:3]([N:10]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([OH:22])=[N:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.I[CH2:24][CH3:25].O>CN(C)C=O>[CH2:3]([N:10]1[CH:14]=[C:13]([CH2:15][CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:12]([O:22][CH2:24][CH3:25])=[N:11]1)[C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

6

Edukt 4

HCID 962WaterHCID 6340IodoethaneHCID 24758Sodium hydrideHCID 178471111HCID 178471111, Verbindung

Produkt 1

HCID 23024912ethyl 3-(1-benzyl-3-ethoxy-1H-pyrazol-4-yl)propionateAusbeute 91 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Sodium hydride (60%, oily, 1.28 g) was added to a solution of ethyl 3-(1-benzyl-3-hydroxy-1H-pyrazol-4-yl)propionate (8.78 g) in N,N-dimethylformamide (100 ml) at 0° C., and the mixture was stirred for 30 minutes. Iodoethane (2.82 ml) was added to the reaction mixture, and the mixture was stirred at room temperature for one hour. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with 1N hydrochloric acid and then with saturated aqueous sodium chloride solution, dried (MgSO4), and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-(1-benzyl-3-ethoxy-1H-pyrazol-4-yl)propionate (8.80 g, yield: 91%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:5, volume ratio).

Aufarbeitung

  1. stirringthe mixture was stirred at room temperature for one hour
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with 1N hydrochloric acid
  4. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-eda984ef5ea74a5086b091333cb88066
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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