Diisobutylaluminum hydride → HCID 18449044, compound

HRID 645955Notes

Reaction equation

HRID 645955 reaction equation
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

Participants

4

Reactant 2

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

Product 1

HCID 18449044HCID 18449044, compoundYield 112.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

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 1 M 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.

Workup

  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)

Sources & evidence

ORD record
ord-5c1e593f319a4889acfa1af567754aa3
Source dataset
uspto-grants-2010_04
Patent number
US07705029B2

Reaction notes

Loading…