Hydrogen Peroxide → 5-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)-1-pentanol

HRID 550533Notes

Reaction equation

HRID 550533 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]=[CH2:17].B1C2CCCC1CCC2.[OH-:27].[Na+].OO>C1COCC1>[CH3:1][N:2]1[C:6]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:5][N:4]=[C:3]1[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][OH:27]

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 789669-Borabicyclo(3.3.1)nonane2×HCID 576918864-methyl-3-(4-penten-1-yl)-5-phenyl-4H-1,2,4-triazole

Product 1

HCID 576918515-(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)-1-pentanol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 4-methyl-3-(4-penten-1-yl)-5-phenyl-4H-1,2,4-triazole (200 mg, 0.88 mmol) in THF (1 mL) was added 9-BBN (0.5M in THF, 1.76 mmol) and the solution was refluxed for 2 h. Two more portions of 9-BBN (0.88 mmol) were added, each after 1 h. The reaction mixture was cooled down at 0 C and was added NaOH (3M, 21Mmol) in one portion followed by dropwise addition of H2O2 (33% in water, 21Mmol). The mixture was stirred for another 2 h at r.t.

Workup

  1. temperaturethe solution was refluxed for 2 h
  2. temperatureThe reaction mixture was cooled down at 0 C

Sources & evidence

ORD record
ord-fa7e811b08824afc96343a5e39696812
Source dataset
uspto-grants-2011_05
Patent number
US07947683B2

Reaction notes

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