Ammonium Chloride → alpha-(1-Methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol

HRID 1089167

Reaktionsgleichung

Reaktionsgleichung von HRID 1089167
C([Li])CCC.[CH3:6][N:7]1[CH:11]=[CH:10][CH:9]=[N:8]1.[Cl:12][C:13]1[C:20]([Cl:21])=[C:19]([O:22][CH3:23])[C:18]([O:24][CH3:25])=[CH:17][C:14]=1[CH:15]=[O:16].[Cl-].[NH4+]>CCCCCC.O1CCCC1>[CH3:6][N:7]1[C:11]([CH:15]([OH:16])[C:14]2[CH:17]=[C:18]([O:24][CH3:25])[C:19]([O:22][CH3:23])=[C:20]([Cl:21])[C:13]=2[Cl:12])=[CH:10][CH:9]=[N:8]1

Komponenten

7

Edukt 4

HCID 25517Ammonium ChlorideHCID 702551H-Pyrazole, 1-methyl-HCID 147486342,3-Dichloro-4,5-dimethoxybenzaldehydeHCID 178418339Butyllithium

Produkt 1

HCID 14748635alpha-(1-Methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcoholAusbeute 90,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8058HexaneLösungsmittel

Versuchsvorschrift

18 ml of 1.6M n-butyl lithium in n-hexane is added dropwise to a solution of 2.26 g of 1-methyl-pyrazole in tetrahydrofuran at -60° C. under argon gas atmosphere and the mixture is stirred at the same temperature for 1 hour. A solution of 5.88 g of 2,3-dichloro-4,5-dimethoxybenzaldehyde in tetrahydrofuran is added dropwise to the mixture at -60° to -50° C. and the mixture is stirred at -50° C. to room temperature for 1 hour. An aqueous ammonium chloride solution is added to the reaction mixture and the mixture is concentrated to remove organic solvent. The residue is extracted with ethyl acetate, and the extract is washed, dried and evaporated to remove solvent. The residue is crystallized from isopropyl ether to give 7.18 g of α-(1-methylpyrazol-5-yl)-2,3-dichloro-4,5-dimethoxybenzylalcohol.

Aufarbeitung

  1. stirringthe mixture is stirred at -50° C. to room temperature for 1 hour
  2. concentrationthe mixture is concentrated
  3. customto remove organic solvent
  4. extractionThe residue is extracted with ethyl acetate
  5. washthe extract is washed
  6. customdried
  7. customevaporated
  8. customto remove solvent
  9. customThe residue is crystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-06102864382144748159a39cb0e918f3
Quelldatensatz
uspto-grants-1990_10
Patentnummer
US04965282

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