Imidazole → 3-{[tert-Butyl(dimethyl)silyl]oxy}benzonitrile

HRID 1352002Notes

Reaction equation

HRID 1352002 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1)#[N:2].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16]>CN(C)C=O>[CH3:19][C:18]([Si:15]([CH3:17])([CH3:16])[O:9][C:5]1[CH:4]=[C:3]([CH:8]=[CH:7][CH:6]=1)[C:1]#[N:2])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 133943-CyanophenolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 226614893-{[tert-Butyl(dimethyl)silyl]oxy}benzonitrileYield 92%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-cyanophenol (5 g, 42 mmol) and imidazole (6.3 g, 92 mmol) in N,N-dimethylformamide (85 mL) at 0° C. was added tert-butyldimethylsilylchloride (7.6 g, 50 mmol). After 10 min, the reaction was warmed to room temperature and stirred for 24 h. The solvent was removed under vacuum. The residual oil was diluted with water (100 mL) and extracted with ether (300 mL). The ether layer was back-extracted with water (3×100 mL) and brine (100 mL), dried (MgSO4) and filtered. Concentration and flash chromatography (silica, 50% ethyl acetate in petroleum ether) afforded 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzonitrile (9 g, 92%) as an oil.

Workup

  1. customThe solvent was removed under vacuum
  2. additionThe residual oil was diluted with water (100 mL)
  3. extractionextracted with ether (300 mL)
  4. extractionThe ether layer was back-extracted with water (3×100 mL) and brine (100 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationConcentration and flash chromatography (silica, 50% ethyl acetate in petroleum ether)

Sources & evidence

ORD record
ord-808a371d0be04f619c2727f0df2e1c1c
Source dataset
uspto-grants-2007_05
Patent number
US07217728B2

Reaction notes

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