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

HRID 1968035Notes

Reaction equation

HRID 1968035 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-5ab76c3699fe4f1a981d5c30acb854fb
Source dataset
uspto-grants-2013_04
Patent number
US08420650B2

Reaction notes

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