Toluene → {5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazol-3-yl}methanol

HRID 733138Notes

Reaction equation

C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[N:8]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][C:25]([F:28])([F:27])[F:26])[CH:15]=[CH:16][CH:17]=2)[N:7]=1)=O)C.CC(C[AlH]CC(C)C)C.C1(C)C=CC=CC=1.[O-]S([O-])(=O)=O.[Mg+2].[NH4+].[Cl-]>ClCCl.CO>[CH3:11][C:9]1[N:8]([C:12]2[CH:13]=[C:14]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=3[O:24][C:25]([F:27])([F:28])[F:26])[CH:15]=[CH:16][CH:17]=2)[N:7]=[C:6]([CH2:4][OH:3])[CH:10]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of ethyl-5-methyl-1-[2′-(trifluoromethoxy)-1,1′-biphenyl-3-yl]1H-pyrazole-3-carboxylate (EXAMPLE 3) (1.1 g, 2.82 mmol) in anhydrous dichloromethane (10 mL) was added DIBAL-H in toluene solution (1.0M, 6.8 mL, 6.8 mmol). The reaction was stirred at 0° C. for 30 minutes, then 0.5 mL of methanol was added. The reaction was warmed up to room temperature, and stirred continuously for another 30 minutes. After the addition of 5 g of Celite and 5 g of anhydrous MgSO4, the saturated NH4Cl aqueous was added dropwise. The resulting slurry was stirred vigorously for an hour. Then the mixture was filtered and concentrated to give the crude product. The crude alcohol obtained was purified by flash-column chromatography on silica-gel to provide the pure titled product as a yellow oil (0.9 g, 93% yield).

Workup

temperatureThe reaction was warmed up to room temperature
stirringstirred continuously for another 30 minutes
stirringThe resulting slurry was stirred vigorously for an hour
filtrationThen the mixture was filtered
concentrationconcentrated
customto give the crude product
customThe crude alcohol obtained
customwas purified by flash-column chromatography on silica-gel

Sources & evidence

ORD record: ord-0c565d32e0ba4d5d861bc8be825b9b95
Source dataset: uspto-grants-2009_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07589116B2

Reaction notes

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