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

HRID 733138노트

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HRID 733138 반응식
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

참가 물질

8

반응물 5

HCID 1140TolueneHCID 14487Diisobutylaluminum hydrideHCID 24083Sulfuric acid magnesium salt (1:1)HCID 25517Ammonium ChlorideHCID 11417896Ethyl-5-methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazole-3-carboxylate

생성물 1

HCID 11187128{5-Methyl-1-[2'-(trifluoromethoxy)-1,1'-biphenyl-3-yl]-1H-pyrazol-3-yl}methanol수율 93%

시약·촉매·용매 2

HCID 887Methanol용매HCID 6344Dichloromethane용매

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온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-0c565d32e0ba4d5d861bc8be825b9b95
출처 데이터셋
uspto-grants-2009_09
특허 번호
US07589116B2

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