Tetrabutylammonium Fluoride → 1-[4-Hydroxymethyl-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

HRID 242389Notes

Reaction equation

HRID 242389 reaction equation
[Si]([O:18][CH2:19][C:20]1[N:21]=[C:22]([C:34](=[O:36])[CH3:35])[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:33])([CH3:32])[CH3:31])[C:24]=1[CH3:25])(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>C1COCC1.O>[OH:18][CH2:19][C:20]1[N:21]=[C:22]([C:34](=[O:36])[CH3:35])[N:23]([CH2:26][O:27][CH2:28][CH2:29][Si:30]([CH3:32])([CH3:31])[CH3:33])[C:24]=1[CH3:25]

Participants

5

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 710877791-[4-(tert-Butyldiphenylsilyloxymethyl)-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

Product 1

HCID 710871031-[4-Hydroxymethyl-5-methyl-1-(2-trimethylsilylethoxymethyl)-1H-imidazol-2-yl]ethanone

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The compound (11.7 g) obtained in (1) was dissolved in THF (100 mL), followed by addition of TBAF (1.0 M THF solution, 24.7 mL) under stirring, and the stirring was continued for 1 hour. The reaction solution was diluted with water, followed by extraction with ethyl acetate. The combined extract was washed with saturated brine, dried over anhydrous sodium sulfate, and subsequently the solvent was distilled off under reduced pressure. The resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→100%) using amino column (product name: Hi-Flash Column 3 L, manufactured by Yamazen Corporation) to afford the title compound (5.41 g).

Workup

  1. extractionfollowed by extraction with ethyl acetate
  2. extractionThe combined extract
  3. washwas washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationsubsequently the solvent was distilled off under reduced pressure
  6. customThe resulting residue was purified by flash chromatography (ethyl acetate/hexane=10%→100%)

Sources & evidence

ORD record
ord-a8b05a6deb654a04a5b1e1ad30458652
Source dataset
uspto-grants-2014_02
Patent number
US08653126B2

Reaction notes

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