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

HRID 1419927

Reaktionsgleichung

Reaktionsgleichung von HRID 1419927
[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]

Komponenten

6

Edukt 3

HCID 9804-NitrophenolHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chloride

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 142844-(Dimethylamino)pyridineKatalysatorHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

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+).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-f731cdad91b249178cadff74b1ee40cb
Quelldatensatz
uspto-grants-1999_03
Patentnummer
US05889026

Verknüpfte Notizen

Wird geladen…