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

HRID 71152Notes

Reaction equation

HRID 71152 reaction equation
CC(OI1(OC(C)=O)(OC(C)=O)OC(=O)C2C=CC=CC1=2)=O.[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:37]#[C:38][CH2:39][CH2:40][CH2:41][CH2:42][OH:43])[CH:28]=[CH:29][C:30]=1[N:31]1[CH:35]=[N:34][C:33]([CH3:36])=[N:32]1.C(=O)([O-])O.[Na+].S([O-])([O-])(=O)=S.[Na+].[Na+]>C(#N)C>[CH3:23][O:24][C:25]1[CH:26]=[C:27]([C:37]#[C:38][CH2:39][CH2:40][CH2:41][CH:42]=[O:43])[CH:28]=[CH:29][C:30]=1[N:31]1[CH:35]=[N:34][C:33]([CH3:36])=[N:32]1

Participants

6

Reactant 4

HCID 24477Sodium ThiosulfateHCID 159087TriacetoxyperiodinaneHCID 516892Sodium BicarbonateHCID 666088346-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol

Product 1

HCID 866629766-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-ynalYield 75.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Dess-Martin reagent (4.99 g) was added to a mixture of 6-[3-methoxy-4-(3-methyl-1H-1,2,4-triazol-1-yl)phenyl]hex-5-yn-1-ol (2.80 g) in acetonitrile (30 mL) 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 (2.11 g).

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-bdd1574a795c4cae9676f1da1df80b97
Source dataset
uspto-grants-2014_09
Patent number
US08822699B2

Reaction notes

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