2-Methyl-2-butanol → N-benzhydrylidene-N'-(3,5-di-tert-butyl-phenyl)-hydrazine

HRID 74466

反応式

HRID 74466 の反応式
C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.C(O)(CC)(C)C.Br[C:42]1[CH:47]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:45]=[C:44]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:43]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[C:66](=[N:79][NH2:80])([C:73]1[CH:78]=[CH:77][CH:76]=[CH:75][CH:74]=1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1>COCCOC.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:66](=[N:79][NH:80][C:42]1[CH:47]=[C:46]([C:48]([CH3:51])([CH3:50])[CH3:49])[CH:45]=[C:44]([C:52]([CH3:55])([CH3:54])[CH3:53])[CH:43]=1)([C:73]1[CH:74]=[CH:75][CH:76]=[CH:77][CH:78]=1)[C:67]1[CH:72]=[CH:71][CH:70]=[CH:69][CH:68]=1

参加物

8

反応物 5

HCID 64052-Methyl-2-butanolHCID 79304DiphenylmethylidenehydrazineHCID 6201361-Bromo-3,5-di-tert-butylbenzeneHCID 2733832Lithium HexamethyldisilazideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl

生成物 1

HCID 86669219N-benzhydrylidene-N'-(3,5-di-tert-butyl-phenyl)-hydrazine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 80711,2-Dimethoxyethane溶媒2 回

反応条件

温度
60 °C

実験手順

Palladium acetate (8.4 mg, 0.037 mmol) and 2-dicyclohexylphosphino-2′,4′,6′-tri-i-propyl-1,1′-biphenyl (X-PHOS) (35.6 mg, 0.074 mmol) were dissolved in tert-amyl alcohol (10 μl, 0.093 mmol) and anhydrous ethylene glycol dimethyl ether (0.25 ml). The mixture was heated and stirred at 60° C. for five minutes under a nitrogen atmosphere to prepare a catalyst. In a separate reaction container under a nitrogen atmosphere, 1-bromo-3,5-di-t-butyl benzene (501 mg, 1.9 mmol), lithium bis(trimethylsilyl) amide (475 mg, 2.8 mmol), and benzophenone hydrazone (401 mg, 2.0 mmol) were dissolved in anhydrous ethylene glycol dimethyl ether (2.5 ml). Then, a solution containing the prepared catalyst was added thereto. After deaeration, this was heated and stirred at 90° C. for two hours under a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and then concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/5). Thus, N-benzhydrylidene-N′-(3,5-di-tert-butyl-phenyl)-hydrazine was obtained as a yellow amorphous material (699 mg, 97.7%).

後処理

  1. temperatureThe mixture was heated
  2. customto prepare a catalyst
  3. customIn a separate reaction container under a nitrogen atmosphere
  4. additionThen, a solution containing the prepared catalyst
  5. additionwas added
  6. temperatureAfter deaeration, this was heated
  7. stirringstirred at 90° C. for two hours under a nitrogen atmosphere
  8. temperatureThe reaction mixture was cooled to room temperature
  9. concentrationconcentrated under reduced pressure
  10. customThe resulting residue was purified by silica gel column chromatography (hexane/ethyl acetate=100/5)

出典と根拠

ORDレコード
ord-bf913cf0e23b45e882f43ade3f130e66
出典データセット
uspto-grants-2014_09
特許番号
US08829199B2

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