Imidazole → (4-Allyl-5-methoxy-2-nitrobenzyloxy)-t-butyldimethylsilane

HRID 494981Notes

Reaction equation

HRID 494981 reaction equation
[CH2:1]([C:4]1[C:11]([O:12][CH3:13])=[CH:10][C:7]([CH2:8][OH:9])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)[CH:2]=[CH2:3].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:4]1[C:11]([O:12][CH3:13])=[CH:10][C:7]([CH2:8][O:9][Si:22]([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23])=[C:6]([N+:14]([O-:16])=[O:15])[CH:5]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 795Imidazole2×HCID 28928tert-Butyldimethylsilyl chloride2×HCID 576827814-Allyl-5-methoxy-2-nitrobenzyl alcohol

Product 1

HCID 57682929(4-Allyl-5-methoxy-2-nitrobenzyloxy)-t-butyldimethylsilaneYield 95.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

229 mg of 4-allyl-5-methoxy-2-nitrobenzyl alcohol was dissolved in 5 ml of N,N-dimethylformamide. Thereafter, 0.17 g of imidazole and 0.23 g of t-butyldimethylsilyl chloride were added to the reaction solution while cooling on ice. The obtained mixture was stirred at room temperature for 2 hours. Thereafter, 34 mg of imidazole and 46 mg of t-butyldimethylsilyl chloride were further added to the reaction solution. The obtained mixture was stirred at room temperature overnight. The reaction solution was diluted with ethyl acetate and then washed with a saturated ammonium chloride aqueous solution and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 330 mg of the subject compound.

Workup

  1. temperaturewhile cooling on ice
  2. stirringThe obtained mixture was stirred at room temperature overnight
  3. washwashed with a saturated ammonium chloride aqueous solution
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. concentrationconcentrated under a reduced pressure
  6. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-c4aa03e07fbf41439164c39926bfc7bc
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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