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

HRID 907917Notes

Reaction equation

HRID 907917 reaction equation
[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[C:3]1[CH2:8][OH:9]>O1CCCC1.[O-2].[Mn+4].[O-2]>[CH3:1][N:2]1[C:6]([CH3:7])=[N:5][N:4]=[C:3]1[CH:8]=[O:9]

Participants

4

Reactant 1

HCID 18726738(dimethyl-4H-1,2,4-triazol-3-yl)methanol

Product 1

HCID 552536594,5-dimethyl-4H-1,2,4-triazole-3-carbaldehydeYield 66%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of (4,5-dimethyl-4H-1,2,4-triazol-3-yl)methanol (2.48 g, 19.5 mmol) and manganese (IV) oxide (17.8 g, 204.8 mmol) in dry tetrahydrofuran (72 mL) was stirred at room temperature overnight. The mixture was filtered, and the cake washed with dichloromethane (100 mL×3). The combined filtrate was concentrated to give the title compound (1.6 g, yield 66%) as a white solid. 1H-NMR (400 MHz, DMSO-d6) δ (ppm): 2.54 (s, 3H), 3.89 (s, 3H), 10.06 (s, 2H). LC-MS (ESI) m/z: 126 (M+1)+.

Workup

  1. filtrationThe mixture was filtered
  2. washthe cake washed with dichloromethane (100 mL×3)
  3. concentrationThe combined filtrate was concentrated

Sources & evidence

ORD record
ord-4b3ee962176e4848a452cc1b25916942
Source dataset
uspto-grants-2011_09
Patent number
US08012976B2

Reaction notes

Loading…