Imidazole → Hexaethyldisiloxane

HRID 1870589Notes

Reaction equation

HRID 1870589 reaction equation
N1[CH:5]=[CH:4]N=C1.[CH2:6]([Si:8](Cl)([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].[OH2:14]>CN(C)C=O>[CH2:6]([Si:8]([O:14][Si:8]([CH2:4][CH3:5])([CH2:9][CH3:10])[CH2:6][CH3:7])([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 962WaterHCID 13819Chlorotriethylsilane

Product 1

HCID 70442Hexaethyldisiloxane

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 205 (15 mmol) in dimethylformamide (30 mL) is cooled to 0° C. and treated with imidazole (30 mmol) and triethylsilyl chloride (20 mmol). The resultant solution is warmed to room temperature. After 12 h, the reaction mixture is poured into 300 mL of water and extracted with ether (3×40 mL). The ethereal extracts are washed with water (2×25 mL) and saturated aqueous brine (25 mL), dried over magnesium sulfate and concentrated in vacuo. The residue is purified by flash chromatography to afford 206.

Workup

  1. extractionextracted with ether (3×40 mL)
  2. washThe ethereal extracts are washed with water (2×25 mL) and saturated aqueous brine (25 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by flash chromatography

Sources & evidence

ORD record
ord-9c5e481612374ec59d0b2557dd10087c
Source dataset
uspto-grants-2000_08
Patent number
US06096904

Reaction notes

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