Sodium hydride → HCID 15008609, compound

HRID 654865Notes

Reaction equation

HRID 654865 reaction equation
[H-].[Na+].[Cl:3][C:4]1[CH:9]=[C:8]([Cl:10])[CH:7]=[CH:6][C:5]=1[C:11]([OH:28])([C:18]([CH3:27])([CH3:26])[CH:19](OS(C)(=O)=O)[CH3:20])[CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1>CN(C)C=O>[Cl:3][C:4]1[CH:9]=[C:8]([Cl: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:18]([CH3:26])([CH3:27])[CH:19]([CH3:20])[O:28]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 19886498HCID 19886498, compound

Product 1

HCID 15008609HCID 15008609, compoundYield 71.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

84 mg (2.1 mmole) of sodium hydride (as a 60% w/w suspension in mineral oil) were added to a solution of 400 mg (0.95 mmole) of 2-(2,4-dichlorophenyl)-3,3-dimethyl-4-mesyloxy-1-(1H-1,2,4-triazol-1-yl)-2-pentanol in 5 ml of N,N-dimethylformamide, and then the mixture was stirred at 90° C. for 2 hours. At the end of this time, the reaction mixture was allowed to cool, after which it was poured into ice-water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous sodium sulfate, after which the solvent was removed by distillation under reduced pressure. The residue was washed with hexane to give 262.4 mg of a crude product, which was then purified by column chromatography through silica gel, eluted with a 1:1 by volume mixture of hexane and ethyl acetate, to afford 220.7 mg (yield 71.4%) of the title compound, melting at 118°-125° C. This compound is a steroisomer, isomeric at the C4 position, of the compound obtained in Example 42.

Workup

  1. temperatureto cool
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customafter which the solvent was removed by distillation under reduced pressure
  6. washThe residue was washed with hexane
  7. customto give 262.4 mg of a crude product, which
  8. customwas then purified by column chromatography through silica gel
  9. washeluted with a 1:1 by volume mixture of hexane and ethyl acetate

Sources & evidence

ORD record
ord-ab335b4f381c41eaa6f2327eb6bd9585
Source dataset
uspto-grants-1992_07
Patent number
US05134152

Reaction notes

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