Imidazole → tert-Butyl(2-iodoethoxy)dimethylsilane

HRID 874795Notes

Reaction equation

HRID 874795 reaction equation
[I:1][CH2:2][CH2:3][OH:4].N1C=CN=C1.[Si:10](Cl)([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]>ClCCl>[I:1][CH2:2][CH2:3][O:4][Si:10]([C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 12225IodoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 2-iodoethanol (17.2 g; 100 mmol) and imidazole (8.17 g; 120 mmol) in dichloromethane (100 mL) was added tert-butyldimethylsilyl chloride (15.83 g; 105 mmol) at such a rate that the reaction temperature did not rise above 30° C. Upon complete addition the solution was left stirring for 17 h, then washed with water (2×50 mL) and brine (50 mL) and dried over MgSO4. Evaporation of the solvent afforded the target compound (28.0 g; 97.8 mmol; 98%) as a colourless liquid.

Workup

  1. customdid not rise above 30° C
  2. additionUpon complete addition the solution
  3. waitwas left
  4. washwashed with water (2×50 mL) and brine (50 mL)
  5. dry with materialdried over MgSO4
  6. customEvaporation of the solvent
  7. customafforded the target compound (28.0 g; 97.8 mmol; 98%) as a colourless liquid

Sources & evidence

ORD record
ord-c991d66b82bb4d1ab7e5d527662933e1
Source dataset
uspto-grants-2015_03
Patent number
US08980956B2

Reaction notes

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