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

HRID 500796Notes

Reaction equation

HRID 500796 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-c09c286d156c44bdb3b4d7d1453c64da
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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