Imidazole → 1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazole

HRID 1885830Notes

Reaction equation

HRID 1885830 reaction equation
[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][O:5][CH2:6]Cl.[NH:10]1[CH:14]=[CH:13][N:12]=[CH:11]1>C1(C)C=CC=CC=1>[CH3:1][Si:2]([CH3:9])([CH3:8])[CH2:3][CH2:4][O:5][CH2:6][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 110526051-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazoleYield 321.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 2-(trimethylsilyl)ethoxymethyl chloride (11.6 g, 0.07 moles), imidazole (9.5 g, 0.014 moles) and dry toluene (100 ml) was stirred at room temperature for 18 hours, and the resulting imidazole hydrochloride was removed by filtration. The filtrate was concentrated to provide 13.4 g (97%) of crude product. Kugelrohr distillation at 94°-100° C. (0.2 mm) gave 8.92 g (65%) of the desired product as a colorless liquid.

Workup

  1. customthe resulting imidazole hydrochloride was removed by filtration
  2. concentrationThe filtrate was concentrated
  3. customto provide 13.4 g (97%) of crude product
  4. distillationKugelrohr distillation at 94°-100° C. (0.2 mm)

Sources & evidence

ORD record
ord-7827e7c52da548529f82237e2f4327de
Source dataset
uspto-grants-1992_09
Patent number
US05147863

Reaction notes

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