Sodium Thiosulfate → 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-one

HRID 71154Notes

Reaction equation

HRID 71154 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[Cl:23][C:24]1[CH:25]=[C:26]([CH:31]([OH:51])[CH2:32][CH2:33][CH2:34][C:35]#[C:36][C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH:47]=[N:46][C:45]([CH3:48])=[N:44]3)=[C:39]([O:49][CH3:50])[CH:38]=2)[CH:27]=[CH:28][C:29]=1[Cl:30].C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>CS(C)=O.C(#N)C>[Cl:23][C:24]1[CH:25]=[C:26]([C:31](=[O:51])[CH2:32][CH2:33][CH2:34][C:35]#[C:36][C:37]2[CH:42]=[CH:41][C:40]([N:43]3[CH:47]=[N:46][C:45]([CH3:48])=[N:44]3)=[C:39]([O:49][CH3:50])[CH:38]=2)[CH:27]=[CH:28][C:29]=1[Cl:30]

Participants

7

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 666089951-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

Product 1

HCID 666084331-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-oneYield 94.7%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6342AcetonitrileSolvent

Procedure

Dess-Martin reagent (248 mg) was added to a mixture of 1-(3,4-dichlorophenyl)-6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol (210 mg), acetonitrile (2.1 mL) and DMSO (200 μL) under ice-cooling, and the mixture was stirred at room temperature for 1 hr. Saturated aqueous sodium hydrogen carbonate solution and saturated aqueous sodium thiosulfate solution were added, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine, and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (198 mg).

Workup

  1. temperaturecooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

Sources & evidence

ORD record
ord-e89717aac73e494fab49add6423a75a6
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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