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

HRID 47599

Reaction equation

HRID 47599 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 12992941Tert-butyl(2-methoxy-5-nitrophenoxy)dimethylsilaneYield 78.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8a008bd90e9c463d915f3845e30dae6e
Source dataset
uspto-grants-2004_03
Patent number
US06699890B2

Linked notes

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