Imidazole → Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilane

HRID 47599

Reaktionsgleichung

Reaktionsgleichung von HRID 47599
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([N+:9]([O-:11])=[O:10])=[CH:5][C:4]=1[OH:12].N1C=CN=C1.[Si:18](Cl)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]>CN(C=O)C>[Si:18]([O:12][C:4]1[CH:5]=[C:6]([N+:9]([O-:11])=[O:10])[CH:7]=[CH:8][C:3]=1[O:2][CH3:1])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Komponenten

5

Edukt 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 694712-Methoxy-5-nitrophenol

Produkt 1

HCID 12992941Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilaneAusbeute 78,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a mixture of 2-methoxy-5-nitrophenol (1.53 g, 9.0 mmol) and imidazole (1.08 g, 15.9 mmol) in anhydrous DMF (40 mL) was added, with stirring, tert-butyldimethylsilyl chloride (2.05 g, 13.6 mmol) and the mixture was allowed to stir at room temperature for 16 h. The solvent was removed in vacuo and the residue was dissolved in 40 mL of 50% ethyl acetate in hexanes and filtered through 10 g of silica gel. The silica gel was washed with an additional 200 mL of 50% ethyl acetate in hexanes and the filtrates were combined and concentrated in vacuo to give 2.01 g of product as a tan crystalline solid. 1H NMR (CDCl3) δ 7.89 (dd, 1H, J=9.0 Hz, 2.8 Hz), 7.69 (d, 1H, J=2.8 Hz), 6.88 (d, 1H, J=9.0), 3.90 (s, 3H), 1.00 (s, 9H), 0.18 (s, 6H).

Aufarbeitung

  1. additionwas added
  2. stirringto stir at room temperature for 16 h
  3. customThe solvent was removed in vacuo
  4. dissolutionthe residue was dissolved in 40 mL of 50% ethyl acetate in hexanes
  5. filtrationfiltered through 10 g of silica gel
  6. washThe silica gel was washed with an additional 200 mL of 50% ethyl acetate in hexanes
  7. concentrationconcentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-8a008bd90e9c463d915f3845e30dae6e
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699890B2

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