Sodium hydride → HCID 22269286, compound

HRID 488902Notes

Reaction equation

HRID 488902 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[CH3:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[C:14]1[CH:21]=[CH:20][C:17]([CH:18]=[O:19])=[CH:16][CH:15]=1>CS(C)=O.O>[CH3:8][N:9]1[CH:13]=[CH:12][N:11]=[C:10]1[C:14]1[CH:21]=[CH:20][C:17]([CH:18]2[CH2:4][O:19]2)=[CH:16][CH:15]=1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 22269273HCID 22269273, compound

Product 1

HCID 22269286HCID 22269286, compoundYield 52.1%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent3×HCID 962WaterSolvent

Procedure

To a suspension of 0.045 g (1.1 mmol) of sodium hydride in DMSO (2 mL) was added a 0.225 g (1.10 mmol) of trimethylsulfonium iodide as a solution in DMSO (2 mL). The mixture was allowed to stir at room temperature for 10 min then a solution of 0.100 g (0.537 mmol) of the above aldehyde in DMSO (1 mL) was added dropwise. The mixture was stirred at room temperature for 4 h then diluted with H2O and washed with EtOAc. The combined organic phase was washed with H2O, dried over anhydrous Na2SO4 and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.056 g (52.1%) of 1-methyl-2-(4-oxiranyl-phenyl)-1H-imidazole as a yellow oil.

Workup

  1. stirringThe mixture was stirred at room temperature for 4 h
  2. washwashed with EtOAc
  3. washThe combined organic phase was washed with H2O
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-174c95c863fd4707935b421ddf04c354
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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