Diisobutylaluminum hydride → HCID 18449044, Verbindung

HRID 1270084Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1270084
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([O:16][CH:17]([F:19])[F:18])=[CH:14][C:13]([C:20]([F:23])([F:22])[F:21])=[N:12]2)=[CH:7][CH:6]=1)C.CC(C[AlH]CC(C)C)C>C1(C)C=CC=CC=1>[F:19][CH:17]([F:18])[O:16][C:15]1[N:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=2)[N:12]=[C:13]([C:20]([F:23])([F:22])[F:21])[CH:14]=1

Komponenten

4

Edukt 2

HCID 14487Diisobutylaluminum hydrideHCID 686934484-(5-Difluoromethoxy-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid ethyl ester

Produkt 1

HCID 18449044HCID 18449044, VerbindungAusbeute 112,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

A solution of 4-(5-difluoromethoxy-3-trifluoromethyl-pyrazol-1-yl)-benzoic acid ethyl ester (0.4 g, 1.1 mmol) in dry toluene (8.0 mL) was stirred and 1M solution of DIBAL-H in toluene (1.33 mL, 1.33 mmol) was added. The resultant solution was stirred at room temperature for 10 minutes. The mixture was quenched with saturated aqueous NH4Cl (40 mL) and extracted with EtOAc (3×40 mL). The organics were washed with water and brine. The solvent was removed under reduced pressure and purification of the resulting residue by chromatography (SiO2, 10:1 Hexane/EtOAc) gave [4-(5-difluoromethoxy-3-trifluoromethyl-pyrazol-1-yl)-phenyl]-methanol (380 mg, 99% yield) as a syrup.

Aufarbeitung

  1. customThe mixture was quenched with saturated aqueous NH4Cl (40 mL)
  2. extractionextracted with EtOAc (3×40 mL)
  3. washThe organics were washed with water and brine
  4. customThe solvent was removed under reduced pressure and purification of the resulting residue by chromatography (SiO2, 10:1 Hexane/EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-947ace617d714d85969ebbdb176e4456
Quelldatensatz
uspto-grants-2007_04
Patentnummer
US07202232B2

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