Imidazole → tert-Butyldimethyl((4-nitrobenzyl)oxy)silane

HRID 565853Notes

Reaction equation

HRID 565853 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][OH:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].[C:12]([Si:16](Cl)([CH3:18])[CH3:17])([CH3:15])([CH3:14])[CH3:13].N1C=CN=C1.CN(C=O)C>O>[C:12]([Si:16]([CH3:18])([CH3:17])[O:9][CH2:8][C:7]1[CH:6]=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:11][CH:10]=1)([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 6228DimethylformamideHCID 28928tert-Butyldimethylsilyl chlorideHCID 692754-Nitrobenzyl alcohol

Product 1

HCID 11065418tert-Butyldimethyl((4-nitrobenzyl)oxy)silaneYield 100.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 4-nitrobenzylalcohol (10.0 g), tertbutyl-dimethylsilyl chloride (11.8 g), imidazole (11.2 g) and DMF (50 ml) was stirred at room temperature for 1.5 hours. To the mixture was added water (500 ml), and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated sodium chloride solution, dried with anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was separated and purified with column chromatography (ethyl acetate/hexane=1/7) to give tert-butyldimethyl-4-nitrobenzyloxysilane (17.5 g) as pale yellow oil.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated sodium chloride solution
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was separated
  6. custompurified with column chromatography (ethyl acetate/hexane=1/7)

Sources & evidence

ORD record
ord-b553beec92154e0c9141f6aafdb292f0
Source dataset
uspto-grants-2001_01
Patent number
US06172061B2

Reaction notes

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