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

HRID 1710936Notes

Reaction equation

HRID 1710936 reaction equation
[H-].[Na+].[NH:3]1[CH:7]=[CH:6][N:5]=[CH:4]1.Cl[CH2:9][O:10][CH2:11][CH2:12][Si:13]([CH3:16])([CH3:15])[CH3:14].CO.CCOC(C)=O>C1COCC1>[CH3:14][Si:13]([CH3:16])([CH3:15])[CH2:12][CH2:11][O:10][CH2:9][N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 21584119Ethylacetate methanol

Product 1

HCID 110526051-((2-(Trimethylsilyl)ethoxy)methyl)-1H-imidazoleYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred suspension of NaH (60% dispersion in oil, 0.65 g, 16.2 mmol) at 0° C. was added imidazole (1 g, 14.7 mmol) in THF (14 mL). The mixture was warmed to room temperature over 30 min, then re-cooled to 0° C. followed by an addition of (2-(chloromethoxy)ethyl)trimethylsilane (2.73 ml, 15.4 mmol). The combined mixture was warmed to room temperature over 1 h, quenched with saturated aqueous ammonium chloride, concentrated to dryness and partitioned between water and EtOAc. Organic phase was collected, dried over anhydrous sodium sulfate, filtered and evaporated. The residue was purified by column chromatography (eluents EtOAc, then MeOH/EtOAc 20:80), to afford the title compound (2.04 g, 70% yield) as a white solid. MS (m/z) 199.3 (M+H).

Workup

  1. temperaturere-cooled to 0° C.
  2. temperatureThe combined mixture was warmed to room temperature over 1 h
  3. customquenched with saturated aqueous ammonium chloride
  4. concentrationconcentrated to dryness
  5. custompartitioned between water and EtOAc
  6. customOrganic phase was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by column chromatography (eluents EtOAc

Sources & evidence

ORD record
ord-3a61f956058b44edb9181250f474f1ba
Source dataset
uspto-grants-2010_09
Patent number
US07790729B2

Reaction notes

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