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

HRID 733138ノート

反応式

HRID 733138 の反応式
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

参加物

8

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-0c565d32e0ba4d5d861bc8be825b9b95
出典データセット
uspto-grants-2009_09
特許番号
US07589116B2

反応ノート

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