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

HRID 74466
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 74466
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
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 167845palladium(II) acetateKatalysatorHCID 80711,2-DimethoxyethaneLösungsmittel2×

Reaktionsbedingungen

Temperatur
60 °C

Versuchsvorschrift

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%).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-bf913cf0e23b45e882f43ade3f130e66
Quelldatensatz
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08829199B2

Notizen zur Reaktion

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