2-t-Butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)propenyl]-1-nitrobenzene → 2-t-Butyl-5-(3-t-butyldimethylsilyloxypropyl)aniline

HRID 1637499Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1637499
[C:1]([C:5]1[CH:10]=[CH:9][C:8](/[CH:11]=[CH:12]/[CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16])=[CH:7][C:6]=1[N+:22]([O-])=O)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)C.[Pd]>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][O:14][Si:15]([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:16])[CH3:17])=[CH:7][C:6]=1[NH2:22])([CH3:4])([CH3:2])[CH3:3]

Komponenten

5

Edukt 2

HCID 193487852-t-Butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)propenyl]-1-nitrobenzeneHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 193485532-t-Butyl-5-(3-t-butyldimethylsilyloxypropyl)anilineAusbeute 84,9 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

A solution of 16.0 g of 2-t-butyl-5-[(1E)-3-(t-butyldimethylsilyloxy)propenyl]-1-nitrobenzene [prepared as described in step (iv) above] in 800 ml of diethyl ether was stirred at room temperature for 3 hours in the presence of 8.0 g of 10% palladium-on-charcoal under a stream of hydrogen. At the end of this time, the reaction mixture was filtered and the filtrate was freed from the solvent by distillation under reduced pressure . The residue was purified by column chromatography through silica gel, using a 1:10 by volume mixture of ethyl acetate and hexane as the eluent, to give 12.5 g of the title compound as an oily substance.

Aufarbeitung

  1. filtrationAt the end of this time, the reaction mixture was filtered
  2. distillationthe filtrate was freed from the solvent by distillation under reduced pressure
  3. customThe residue was purified by column chromatography through silica gel
  4. additionby volume mixture of ethyl acetate and hexane as the eluent

Quellen und Nachweise

ORD-Eintrag
ord-293f6f32ce8d43db993587861a6e0681
Quelldatensatz
uspto-grants-2000_03
Patentnummer
US06040339

Notizen zur Reaktion

Wird geladen…