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

HRID 1418184Notes

Reaction equation

HRID 1418184 reaction equation
[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]

Participants

5

Reactant 2

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

Product 1

HCID 193485532-t-Butyl-5-(3-t-butyldimethylsilyloxypropyl)anilineYield 84.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 3283Diethyl EtherSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-f77860948e7848a2a5869d1a25f1b731
Source dataset
uspto-grants-1999_03
Patent number
US05880147

Reaction notes

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