Sodium Iodide → tert-Butyl(2-iodoethoxy)dimethylsilane

HRID 637237Notes

Reaction equation

HRID 637237 reaction equation
[Si:1]([O:8][CH2:9][CH2:10]Br)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[I-:12].[Na+]>CC(C)=O.CN(C)C=O>[Si:1]([O:8][CH2:9][CH2:10][I:12])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 5238Sodium IodideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilane

Product 1

HCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilane

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 6228DimethylformamideSolvent

Procedure

Combine 2-(t-butyldimethylsilyloxy)ethyl bromide (116.2 g, 486 mmol), and sodium iodide (100 g, 663 mol) in acetone (350 mL) and dimethylformamide (25 mL). Heat to reflux. After 4 hours, cool, filter and evaporate in vacuo to give a residue. Distill the residue to give 2-(t-butyldimethylsilyloxy)ethyl iodide: bp; 60° C. at 0.5 mm Hg.

Workup

  1. temperatureHeat to reflux
  2. temperaturecool
  3. filtrationfilter
  4. customevaporate in vacuo
  5. customto give a residue
  6. distillationDistill the residue

Sources & evidence

ORD record
ord-f99ed3d55edb440dab82c95de1bd06fa
Source dataset
uspto-grants-2001_02
Patent number
US06194406B1

Reaction notes

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