(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)methanol → 4-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehyde

HRID 628693Notes

Reaction equation

HRID 628693 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][OH:14]>C1COCC1.O=[Mn]=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[CH:13]=[O:14]

Participants

4

Reactant 1

HCID 11528485(4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 115428934-methyl-5-phenyl-4H-1,2,4-triazole-3-carbaldehydeYield 64%

Reagents, catalysts & solvents 2

HCID 14801Manganese dioxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of (4-methyl-5-phenyl-4H-1,2,4-triazol-3-yl)methanol, 35, (1.3 g, 6.9 mmol) in THF (20 mL) was added MnO2 (6.0 g, 68.7 mmol). The reaction stirred at room temperature for 2 h. The reaction mixture was then filtered through a plug of Celite® and concentrated in vacuo. The crude material was purified via silica gel chromatography (0-5% methanol/dichloromethane) yielding 820 mg (64%) of 36: 1H NMR (400 MHz, CDCl3) δ 10.14, (s, 1H), 7.68-7.60 (m, 2H), 7.59-7.45, (m, 3H), 3.98 (s, 3H); ESI+ MS: m/z (rel intensity) 188 (100, M+H).

Workup

  1. filtrationThe reaction mixture was then filtered through a plug of Celite®
  2. concentrationconcentrated in vacuo
  3. customThe crude material was purified via silica gel chromatography (0-5% methanol/dichloromethane)

Sources & evidence

ORD record
ord-53ce19972269408a9880ca9cdcd3d15d
Source dataset
uspto-grants-2016_04
Patent number
US09314468B2

Reaction notes

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