Water → 4-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)butanal

HRID 550532Notes

Reaction equation

HRID 550532 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=[C:3]1[CH2:13][CH2:14][CH2:15][CH:16]=C.[OH2:18]>C1COCC1.O.O=[Os](=O)(=O)=O>[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:5][N:4]=[C:3]1[CH2:13][CH2:14][CH2:15][CH:16]=[O:18]

Participants

5

Reactant 2

HCID 962WaterHCID 576918864-methyl-3-(4-penten-1-yl)-5-phenyl-4H-1,2,4-triazole

Product 1

HCID 576919404-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)butanal

Reagents, catalysts & solvents 2

HCID 30318Osmium TetroxideCatalystHCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a solution of 4-methyl-3-(4-penten-1-yl)-5-phenyl-4H-1,2,4-triazole (196 mg, 0.86 mmol) in THF/H2O (7.5/1.5 ml) were added OsO4 (4% solution in water, 0.04 mmol) and NalO4 (2.6 mmol). The solution was stirred o.n. at r.t. Water was added and product was extract with DCM. The organic phase was separated, dried over Na2SO4 and filtered. Volatiles were evaporated in vacuo to give 178 mg of the title compound as an oil, which was used in the subsequent step without further purification.

Workup

  1. customat r.t
  2. extractionproduct was extract with DCM
  3. customThe organic phase was separated
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. customVolatiles were evaporated in vacuo

Sources & evidence

ORD record
ord-c49a722371214ade98e4657b7462a3f9
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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