tert-Butyldimethyl((4-nitrobenzyl)oxy)silane → 4-Aminobenzyloxy-tert-butyldimethylsilane

HRID 2228052Notes

Reaction equation

HRID 2228052 reaction equation
[C:1]([Si:5]([CH3:18])([CH3:17])[O:6][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-])=O)=[CH:10][CH:9]=1)([CH3:4])([CH3:3])[CH3:2]>C(O)C>[NH2:14][C:11]1[CH:12]=[CH:13][C:8]([CH2:7][O:6][Si:5]([C:1]([CH3:2])([CH3:3])[CH3:4])([CH3:17])[CH3:18])=[CH:9][CH:10]=1

Participants

3

Reactant 1

HCID 11065418tert-Butyldimethyl((4-nitrobenzyl)oxy)silane

Product 1

HCID 110754704-Aminobenzyloxy-tert-butyldimethylsilaneYield 94.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In ethanol (80 ml) was dissolved tert-butyldimethyl-4-nitrobenzyloxysilane (16.5 g), and to the mixture was added dried 5% palladium on carbon (0.83 g). Under hydrogen atmosphere, the mixture was stirred at room temperature under atmospheric pressure for 7.5 hours. The palladium was filtered off, and the filtrate was concentrated. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1/4) to give 4-aminobenzyloxy-tert-butyldimethylsilane (13.8 g) as colorless oil.

Workup

  1. additionto the mixture was added
  2. dry with materialdried 5% palladium on carbon (0.83 g)
  3. filtrationThe palladium was filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1/4)

Sources & evidence

ORD record
ord-9090b773a41446c5ad88211c412b1f46
Source dataset
uspto-grants-2002_07
Patent number
US06413947B1

Reaction notes

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