Water → HCID 22269061, compound

HRID 488901Notes

Reaction equation

HRID 488901 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)C.[S:8]1[CH:12]=[CH:11][N:10]=[C:9]1[C:13]1[CH:20]=[CH:19][C:16]([CH:17]=[O:18])=[CH:15][CH:14]=1.O>CS(C)=O>[O:18]1[CH2:4][CH:17]1[C:16]1[CH:15]=[CH:14][C:13]([C:9]2[S:8][CH:12]=[CH:11][N:10]=2)=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 75127Trimethylsulfonium iodideHCID 105356554-(1,3-Thiazol-2-yl)benzaldehyde

Product 1

HCID 22269061HCID 22269061, compoundYield 92.4%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent3×

Procedure

To a suspension of 0.063 g (1.5 mmol) of sodium hydride in DMSO (10 mL) was added 0.300 g (1.47 mmol) of trimethylsulfonium iodide as a solution in DMSO (5 mL). After stirring at room temperature for 5 min 0.130 g (0.687 mmol) of the above aldehyde was added as a solution in DMSO (5 mL). The mixture was allowed to stir at room temperature for 2 h. The mixture was poured into H2O and washed with EtOAc. The combined organic phase was washed with H2O, dried over anhydrous MgSO4 and concentrated under reduced pressure. The residue was purified by flash silica gel chromatography to provide 0.129 g (92.3%) of 2-(4-oxiranyl-phenyl)-thiazole as a clear oil.

Workup

  1. washwashed with EtOAc
  2. washThe combined organic phase was washed with H2O
  3. dry with materialdried over anhydrous MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-91eb7ab83e6c49c89cfbb2c5645f30ad
Source dataset
uspto-grants-2005_12
Patent number
US06974870B2

Reaction notes

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