tert-Butyldimethyl(4-nitrophenoxy)silane → 4-((Tert-butyldimethylsilyl)oxy)aniline

HRID 7237

Reaction equation

HRID 7237 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][Si:11]([CH3:17])([CH3:16])[C:12]([CH3:15])([CH3:14])[CH3:13])=[CH:6][CH:5]=1)([O-])=O>C(OCC)(=O)C.[Pd]>[CH3:17][Si:11]([CH3:16])([O:10][C:7]1[CH:6]=[CH:5][C:4]([NH2:1])=[CH:9][CH:8]=1)[C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

4

Reactant 1

HCID 532659tert-Butyldimethyl(4-nitrophenoxy)silane

Product 1

HCID 117155534-((Tert-butyldimethylsilyl)oxy)aniline

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 1-nitro4-(1,1,2,2-tetramethyl-1-silapropoxy)benzene (7.8 g, 30.8 mmol) (from Example 19a supra) and 10% Pd/C (0.70 g) (Aldrich) in ethyl acetate (100 mL) was hydrogenated for 1 day. The reaction mixture was filtered though Celite® and concentrated. The residue was purified by flash chromatography eluting with ethyl acetate/hexanes (1:9 V/N)) to afford 4-(1,1,2,2-tetramethyl-1-silapropoxy)phenylamine. (Yield 6.7 g, 97%).

Workup

  1. filtrationThe reaction mixture was filtered though Celite®
  2. concentrationconcentrated
  3. customThe residue was purified by flash chromatography
  4. washeluting with ethyl acetate/hexanes (1:9 V/N))

Sources & evidence

ORD record
ord-a803ccb62a404612ad797f6d240d47bb
Source dataset
uspto-grants-2006_08
Patent number
US07084270B2

Linked notes

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