Dimethylformamide → HCID 23021918, Verbindung

HRID 350190Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 350190
[CH2:1]([O:3][C:4]1[C:8]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][NH:6][N:5]=1)[CH3:2].Cl[CH2:17][C:18]1[CH:31]=[CH:30][C:21]([O:22][CH2:23][C:24]2[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=2)=[CH:20][CH:19]=1.CN(C)C=O.[H-].[Na+]>O>[CH2:1]([O:3][C:4]1[C:8]([CH2:9][CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:7][N:6]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:22][CH2:23][C:24]3[CH:25]=[N:26][CH:27]=[CH:28][CH:29]=3)=[CH:30][CH:31]=2)[N:5]=1)[CH3:2]

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 230219333-(4-Chloromethylphenoxymethyl)pyridineHCID 178471163HCID 178471163, Verbindung

Produkt 1

HCID 23021918HCID 23021918, VerbindungAusbeute 55 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 962WaterLösungsmittel

Versuchsvorschrift

To a mixture of ethyl 3-(3-ethoxy-1H-pyrazol-4-yl]propionate (415 mg), 3-(4-chloromethylphenoxymethyl)pyridine (554 mg), and N,N-dimethylformamide (10 ml), sodium hydride (60%, oily, 80.0 mg) was added at 0° C., and then the mixture was stirred at room temperature for 30 minutes. The reaction mixture was poured into water, which was extracted with ethyl acetate. The ethyl acetate layer was washed with water, then, with saturated aqueous sodium chloride solution, dried (MgSO4) and concentrated. The residue was subjected to silica gel column chromatography, and ethyl 3-[3-ethoxy-1-[4-(3-pyridylmethoxy)benzyl]-1H-pyrazol-4-yl]propionate (340 mg, yield: 55%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Aufarbeitung

  1. additionwas added at 0° C.
  2. extractionwas extracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with water
  4. dry with materialwith saturated aqueous sodium chloride solution, dried (MgSO4)
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-53f79e48258247a08aff8c9d1c3697e8
Quelldatensatz
uspto-grants-2007_02
Patentnummer
US07179823B1

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