Sodium hydride → 1-(2-Trimethylsilanylethoxymethyl)-1H -imidazole-4-carbaldehyde

HRID 497563Notes

Reaction equation

HRID 497563 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1.[H-].[Na+].[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15]Cl>CN(C)C=O>[CH3:10][Si:11]([CH3:18])([CH3:17])[CH2:12][CH2:13][O:14][CH2:15][N:1]1[CH:5]=[C:4]([CH:6]=[O:7])[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 764281H-Imidazole-4-carbaldehydeHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether

Product 1

HCID 119910021-(2-Trimethylsilanylethoxymethyl)-1H -imidazole-4-carbaldehydeYield 77%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Imidazole-4-carboxaldehyde (1 g, 10.4 mmol) was added portionwise to a solution of sodium hydride (463 mg, 60% dispersion in mineral oil, 11.4 mmol) in N,N-dimethylformamide (15 ml), and the solution stirred for 30 minutes at room temperature. 2-(Trimethylsilyl)ethoxymethyl chloride (2.03 ml, 11.4 mmol) was added and the reaction stirred at room temperature for 18 hours. The reaction was quenched by the addition of aqueous ammonium chloride solution, and the mixture extracted with ethyl acetate (2×). The combined organic extracts were dried (Na2SO4), filtered, and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with methanol:ethyl acetate (3:97), to give the title compound, 1.8 g, 77% yield.

Workup

  1. stirringthe reaction stirred at room temperature for 18 hours
  2. customThe reaction was quenched by the addition of aqueous ammonium chloride solution
  3. extractionthe mixture extracted with ethyl acetate (2×)
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by column chromatography on silica gel
  8. washeluting with methanol:ethyl acetate (3:97)

Sources & evidence

ORD record
ord-9977f757f033408fbe2c977d69262a74
Source dataset
uspto-grants-2005_09
Patent number
US06949577B2

Reaction notes

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