Iodoethanol → tert-Butyl(2-iodoethoxy)dimethylsilane

HRID 1585949Notes

Reaction equation

HRID 1585949 reaction equation
[I:1][CH2:2][CH2:3][OH:4].CN(C1C=CC=CN=1)C.C(N(C(C)C)CC)(C)C.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl>[C:26]([Si:23]([O:4][CH2:3][CH2:2][I:1])([CH3:25])[CH3:24])([CH3:29])([CH3:28])[CH3:27]

Participants

6

Reactant 4

HCID 12225IodoethanolHCID 218852-DimethylaminopyridineHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531Diisopropylethylamine

Product 1

HCID 11129873tert-Butyl(2-iodoethoxy)dimethylsilane

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 2-iodoethanol (20 gm, 116 mmol) suspended in methylene chloride (500 mL) was added dimethylaminopyridine (100 mg) followed by diisopropylethylamine (30 mL, 174 mmol) and tert-butyldimethylsilyl chloride (19 gm, 128 mmol). The reaction was stirred overnight and the solvent was removed in vacuo and the residue was passed through a short column of silica gel and eluted with 95:5 methylene chloride: methanol. The desired fractions were combined and the solvent was removed in vacuo to give the desired product.

Workup

  1. customthe solvent was removed in vacuo
  2. washeluted with 95:5 methylene chloride
  3. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-4826baf45ee54fa3a3556519102becc9
Source dataset
uspto-grants-1999_08
Patent number
US05939439

Reaction notes

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