Sodium hydride → HCID 15008587, compound

HRID 654853Notes

Reaction equation

HRID 654853 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([OH:26])([C:17]([CH3:25])([CH3:24])[CH2:18]OS(C)(=O)=O)[CH2:11][N:12]2[CH:16]=[N:15][CH:14]=[N:13]2)=[CH:6][CH:5]=1>CN(C)C=O>[Cl:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]2([CH2:11][N:12]3[CH:16]=[N:15][CH:14]=[N:13]3)[C:17]([CH3:24])([CH3:25])[CH2:18][O:26]2)=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 19886512HCID 19886512, compound

Product 1

HCID 15008587HCID 15008587, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

160 mg of sodium hydride (as a 60% w/w dispersion in mineral oil) were added to a solution of 750 mg of 2-(4-chlorophenyl)-3,3-dimethyl-4-methanesulfonyloxy-1-(1H-1,2,4-triazol-1-yl)-2-butanol in 12 ml of dimethylformamide, and the resulting mixture was stirred at room temperature for 3 hours. At the end of this time, the reaction mixture was poured into ice-water and extracted with ethyl acetate. The extract was washed with an aqueous solution of ammonium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was purified by preparative thin layer chromatography, using a 1:4 by volume mixture of ethyl acetate and hexane as the developing solvent, to afford 170 mg (yield 31%) of the title compound, melting at 90°-102° C.

Workup

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

Sources & evidence

ORD record
ord-9616d681de764535809d73da6cd64f79
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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