Diisobutylaluminum hydride → HCID 18449040, compound

HRID 645958Notes

Reaction equation

HRID 645958 reaction equation
C([O:3][C:4](=O)[C:5]1[CH:10]=[CH:9][C:8]([N:11]2[C:15]([C:16]([F:19])([F:18])[F:17])=[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:23][C:20]([F:21])([F:22])[C:13]1[CH:14]=[C:15]([C:16]([F:17])([F:18])[F:19])[N:11]([C:8]2[CH:7]=[CH:6][C:5]([CH2:4][OH:3])=[CH:10][CH:9]=2)[N:12]=1

Participants

4

Reactant 2

HCID 14487Diisobutylaluminum hydrideHCID 58841918HCID 58841918, compound

Product 1

HCID 18449040HCID 18449040, compoundYield 94.8%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A stirred solution of 4-(3,5-bis-trifluoromethyl-pyrazol-1-yl)-benzoic acid ethyl ester (2.4 g, 6.8 mmol) in dry toluene (20 mL) was treated with 1 M solution of DIBAL-H in toluene (10.2 mL, 10.2 mmol) at room temperature. The mixture was stirred for 1 hour and quenched with saturated aqueous NH4Cl (30 mL). The organic layer was separated and the aqueous layer was extracted with EtOAc (2×30 mL). The organics were washed with water (30 mL), dried (anhydrous Na2SO4) and the solvent removed under reduced pressure. Purification by flash chromatography (SiO2, 4:1 hexane/EtOAc) gave [4-(3, 5-bis-trifluoromethyl-pyrazol-1-yl)-phenyl]-methanol (2 g, 94.8% yield) as a colorless oil.

Workup

  1. customquenched with saturated aqueous NH4Cl (30 mL)
  2. customThe organic layer was separated
  3. extractionthe aqueous layer was extracted with EtOAc (2×30 mL)
  4. washThe organics were washed with water (30 mL)
  5. dry with materialdried (anhydrous Na2SO4)
  6. customthe solvent removed under reduced pressure
  7. customPurification by flash chromatography (SiO2, 4:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-54a02901b73441318ff730d4e7136014
Source dataset
uspto-grants-2010_04
Patent number
US07705029B2

Reaction notes

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