Sodium hydride → 2-(2,4-Difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]oxetane

HRID 654859Notes

Reaction equation

HRID 654859 reaction equation
[H-].[Na+].[I-].[CH3:4][S+](C)(C)=O.[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C:17]1([CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH2:19][O:18]1>CS(C)=O>[F:9][C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[CH:12][C:11]=1[C:17]1([CH2:20][N:21]2[CH:25]=[N:24][CH:23]=[N:22]2)[CH2:19][CH2:4][O:18]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 74498Sulfoxonium, trimethyl-, iodide (1:1)HCID 101309211-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazole

Product 1

HCID 150085882-(2,4-Difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]oxetaneYield 45%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
80 °C

Procedure

101 mg (4.2 mmole) of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to 10 ml of dimethyl sulfoxide, and the resulting mixture was stirred at 80° C. for 30 minutes. At the end of this time, the mixture was cooled, 928 mg (4.2 mmole) of trimethylsulfoxonium iodide were added thereto and the reaction temperature was allowed to rise to room temperature. The mixture was then stirred for 30 minutes, after which 501 mg (2.11 mmole) of 2-(2,4-difluorophenyl)-2-[(1H-1,2,4-triazol-1-yl)methyl]-oxirane was added, and the mixture was stirred at 50° C. for a further 16 hours. At the end of this time, the reaction mixture was cooled, poured into 50 ml of ice-water and extracted with 100 ml of ethyl acetate. The extract was washed with a saturated aqueous solution of sodium chloride, dried over anhydrous sodium sulfate and concentrated by evaporation under reduced pressure. The residue was subjected to column chromatography through silica gel, eluted with a 2:3 by volume mixture of hexane and ethyl acetate, to afford 238 mg (yield 45%.) of the title compound as an oil.

Workup

  1. temperatureAt the end of this time, the mixture was cooled
  2. customto rise to room temperature
  3. stirringThe mixture was then stirred for 30 minutes
  4. stirringthe mixture was stirred at 50° C. for a further 16 hours
  5. temperatureAt the end of this time, the reaction mixture was cooled
  6. extractionextracted with 100 ml of ethyl acetate
  7. washThe extract was washed with a saturated aqueous solution of sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. concentrationconcentrated by evaporation under reduced pressure
  10. washeluted with a 2:3 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-1c41f69793b7431194e4b5d3433c30d2
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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