4-Nitrophenol → tert-Butyldimethyl(4-nitrophenoxy)silane

HRID 1419927

Reaction equation

HRID 1419927 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([OH:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:11]([Si:15](Cl)([CH3:17])[CH3:16])([CH3:14])([CH3:13])[CH3:12].C(N(CC)CC)C>C(Cl)Cl.CN(C)C1C=CN=CC=1>[C:11]([Si:15]([CH3:17])([CH3:16])[O:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)([CH3:14])([CH3:13])[CH3:12]

Participants

6

Reactant 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 532659tert-Butyldimethyl(4-nitrophenoxy)silaneYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

4-Nitrophenol (5.6 g, 40 mmol) was dissolved in CH2Cl2 (200 ml) and stirred at room temperature in the presence of tertbutyldimethyl-silyl chloride (7.8 g, 52 mmol), 4-dimethylaminopyridine (0.1 g, 0.8 mmol) and triethylamine (7.2 ml, 52 mmol). After 30 minutes at room temperature, the reaction mixture was washed with H2O (2×200 ml) and the resulting aqueous phases were extracted with CH2Cl2 (100 ml). The combined organic phases were dried over Na2SO4 and concentrated. The residue was chromatographed over silica gel (hexane-ether 9:1) to provide tert-Butyl-dimethyl-(4-nitro-phenoxy)-silane (10 g, 100%) as a yellow solid, m.p. 36°-38° C. and MS: m/e=253 (M+).

Workup

  1. washthe reaction mixture was washed with H2O (2×200 ml)
  2. extractionthe resulting aqueous phases were extracted with CH2Cl2 (100 ml)
  3. dry with materialThe combined organic phases were dried over Na2SO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed over silica gel (hexane-ether 9:1)

Sources & evidence

ORD record
ord-f731cdad91b249178cadff74b1ee40cb
Source dataset
uspto-grants-1999_03
Patent number
US05889026

Linked notes

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