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

HRID 513853

반응식

HRID 513853 반응식
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

참가 물질

8

반응물 5

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 80711,2-Dimethoxyethane용매2회

반응 조건

온도
60 °C

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ba92a1c034b5427fb5be92a2d8cced97
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09102692B2

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