Sodium hydride → HCID 57010991, compound

HRID 654854Notes

Reaction equation

HRID 654854 reaction equation
[H-].[Na+].[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C:11]([OH:28])([CH:18]([CH3:27])[CH:19](OS(C)(=O)=O)[CH2:20][CH3:21])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1>CN(C)C=O>[F:3][C:4]1[CH:9]=[C:8]([F:10])[CH:7]=[CH:6][C:5]=1[C@@:11]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[C@@H:18]([CH3:27])[C@H:19]([CH2:20][CH3:21])[O:28]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 19886494HCID 19886494, compound

Product 1

HCID 57010991HCID 57010991, compoundYield 22.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

960 mg (0.24 mmole) of sodium hydride (as a 60% w/w dispersion in mineral oil) were added, whilst ice-cooling, to a solution of 77.9 mg (0.2 mmole) of 2-(2,4-difluorophenyl)-4-methanesulfonyloxy-3-methyl-1-(1H-1,2,4-triazol-1-yl)-2-hexanol in 4.9 ml of dimethylformamide. The resulting mixture was then stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into 20 ml of ice-water and extracted with 40 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 purified by preparative thin layer chromatography, using a 2:1 by volume mixture of hexane and ethyl acetate as the developing solvent, to afford 13.0 mg (yield 22.2%) of the title compound as an oil.

Workup

  1. extractionextracted with 40 ml of ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography
  6. additionby volume mixture of hexane and ethyl acetate as the developing solvent

Sources & evidence

ORD record
ord-eca1c225af8c40548273e6ec56d3ca30
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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