Imidazole → Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilane

HRID 1792318Notes

Reaction equation

HRID 1792318 reaction equation
[Cl:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][OH:7].N1C=CN=C1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]>C(#N)C>[Si:13]([O:7][CH2:6][CH2:5][O:4][CH2:3][CH2:2][Cl:1])([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 123612-(Chloroethoxy)ethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 4555750Tert-butyl(2-(2-chloroethoxy)ethoxy)dimethylsilaneYield 92.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of ethylene glycol mono-2-chloroethyl ether (6.2 g, 50 mmol) in acetonitrile (150 mg) were added imidazole (6.77 g, 99.54 mmol) and t-butyldimethylsilyl chloride (11.25 g, 74.65 mmol) at room temperature. The reaction mixture was stirred overnight at the same temperature. After the reaction was completed, the mixture was filtered through a filter paper, and concentrated under reduced pressure. Then, the concentrate was subjected to flash chromatography on silica gel (n-hexane:ethyl acetate=9:1) to give the title compound (11.0 g, yield 92%) as a colorless oil.

Workup

  1. filtrationthe mixture was filtered through a filter paper
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ffdd5cd198f44aaf81452252372484d6
Source dataset
uspto-grants-2006_07
Patent number
US07074819B2

Reaction notes

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