Imidazole → tert-Butyl(2-iodoethoxy)dimethylsilane

HRID 1764979Notes

Reaction equation

HRID 1764979 reaction equation
[I:1][CH2:2][CH2:3][OH:4].N1C=CN=C1.[CH3:10][C:11]([Si:14](Cl)([CH3:16])[CH3:15])([CH3:13])[CH3:12]>ClCCl>[I:1][CH2:2][CH2:3][O:4][Si:14]([C:11]([CH3:13])([CH3:12])[CH3:10])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 12225IodoethanolHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilaneYield 115.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-iodoethanol (3 g, 17 mmol) and imidazole (1.74 g, 25 mmol) in 20 mL anhydrous dichloromethane was added TBSCl (2.82 g, 18.7 mmol). The mixture was stirred at room temperature overnight (12 hours). The reaction mixture was washed with water (2×10 mL), brine (10 mL) and dried over Na2SO4. Removal of the solvent afforded pure product I(CH2)2OTBS (1) (5.6 g, 98% yield, MW: 286.02).

Workup

  1. washThe reaction mixture was washed with water (2×10 mL), brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. customRemoval of the solvent

Sources & evidence

ORD record
ord-96146e104fed41b080defba41d6928c3
Source dataset
uspto-grants-2007_06
Patent number
US07226563B2

Reaction notes

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