Sodium hydride → 4-Bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazole

HRID 1027295Notes

Reaction equation

HRID 1027295 reaction equation
[Br:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.[H-].[Na+].[CH3:9][Si:10]([CH2:13][CH2:14][O:15][CH2:16]Cl)([CH3:12])[CH3:11]>C1COCC1>[Br:1][C:2]1[N:3]=[CH:4][N:5]([CH2:16][O:15][CH2:14][CH2:13][Si:10]([CH3:12])([CH3:11])[CH3:9])[CH:6]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 178418934HCID 178418934, compound

Product 1

HCID 672945484-Bromo-1-[[2-(trimethylsilyl)ethoxy]methyl]-1H-imidazoleYield 72.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a mixture of 4-bromo-1H-imidazole (1.0 g, 6.8 mmol) in THF (15 mL) was added NaH (327 mg, 8.16 mmol) at 0° C. The mixture was stirred at 0° C. to RT for 0.5 h. SEMCl (1.45 mL, 8.16 mmol) was added dropwise and the reaction mixture was stirred at RT for 2 h. The reaction mixture was quenched with water and extracted with DCM. The organic layer was dried (Na2SO4), filtered and concentrated in vacuo to give the crude product which was purified by silica gel chromotography (10-100% EtOAc/Heptane, then 0-15% MeOH/DCM) to afford 4-bromo-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-imidazole (1.36 g, MS: 279.3 [M+H+]).

Workup

  1. stirringthe reaction mixture was stirred at RT for 2 h
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with DCM
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give the crude product which
  8. customwas purified by silica gel chromotography (10-100% EtOAc/Heptane

Sources & evidence

ORD record
ord-4c5299e6a6774b03b93277690e38ec75
Source dataset
uspto-grants-2014_05
Patent number
US08729263B2

Reaction notes

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