Water → HCID 67084484, Verbindung

HRID 595199

Reaktionsgleichung

Reaktionsgleichung von HRID 595199
C([O-])([O-])=O.[Cs+].[Cs+].[Br:7][C:8]1[CH:9]=[N:10][NH:11][CH:12]=1.Cl[CH2:14][CH:15]1[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]1.O>CN(C=O)C.CCOC(C)=O>[Br:7][C:8]1[CH:9]=[N:10][N:11]([CH2:14][CH:15]2[CH2:19][O:18][C:17]([CH3:21])([CH3:20])[O:16]2)[CH:12]=1

Komponenten

7

Edukt 4

HCID 962WaterHCID 10796Cesium carbonateHCID 163754-BromopyrazoleHCID 203744-(Chloromethyl)-2,2-dimethyl-1,3-dioxolane

Produkt 1

HCID 67084484HCID 67084484, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
65 °C

Versuchsvorschrift

Cs2CO3 (5.3 g, 16.3 mmol) was added to a solution of 4-bromo-1H-pyrazole (2 g, 13.6 mmol) in DMF (10 mL), followed by 4-(chloromethyl)-2,2-dimethyl-1,3-dioxolane (2.46 g, 16.3 mmol) and the resulting mixture heated to an internal temperature of 65° C. After stirring for 14 h, water and EtOAc was added and the layers separated. The organic layer was washed a second time with water, dried with over anhydorus magnesium sulfate, filtered and concentrated under reduced pressure. The resulting crude residue was absorbed on silica gel and purified by column chromatography on silica (0 to 100% EtOAc/Hex) to afford 4-bromo-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)-1H-pyrazole as a light yellow oil, MS ESI calcd. for C9H14BrN2O2 [M+H]+ 261. found 261.

Aufarbeitung

  1. customthe layers separated
  2. washThe organic layer was washed a second time with water
  3. dry with materialdried with over anhydorus magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe resulting crude residue was absorbed on silica gel
  7. custompurified by column chromatography on silica (0 to 100% EtOAc/Hex)

Quellen und Nachweise

ORD-Eintrag
ord-ab9489696be3469d873d56cce9da4507
Quelldatensatz
uspto-grants-2016_01
Patentnummer
US09242984B2

Verknüpfte Notizen

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