Dimethylformamide → HCID 67792622, compound

HRID 654860Notes

Reaction equation

HRID 654860 reaction equation
[H-].[Na+].[C:3]1([CH:9](O)[CH2:10][N:11]2[CH:15]=[N:14][CH:13]=[N:12]2)[CH:8]=[CH:7][CH:6]=[CH:5]C=1.CN(C)[CH:19]=[O:20]>>[C:9]1([C:9]2([CH2:10][N:11]3[CH:15]=[N:14][CH:13]=[N:12]3)[CH2:3][CH2:8][C:7]32[CH2:6][CH2:5]3)[CH:3]=[CH:8][CH2:7][O:20][CH:19]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 10081198HCID 10081198, compound

Product 1

HCID 67792622HCID 67792622, compoundYield 9.9%

Procedure

33.2 mg (0,496 mmole) of sodium hydride (as a 60% w/w dispersion in mineral oil) was added, whilst ice-cooling, to a solution of 69.8 mg (0.207 mmole) of 1-[1-methanesulfonyloxymethyl)cyclopropan-1-yl]-1-phenyl-2-(1H-1,2,4-triazol-1-yl)ethanol in dimethylformamide, and the resulting mixture was stirred at room temperature for 2 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 a saturated aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and concentrated by evaporation under reduced pressure. The resulting residue was subjected to column chromatography through silica gel, eluted with a 1:1 by volume mixture of hexane and ethyl acetate, to afford 5 mg (yield 9.9%) of the title compound as an oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous solution of sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated by evaporation under reduced pressure
  5. washeluted with a 1:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-6f1deba2aaa847d98f401030cf693326
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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