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

HRID 1467655Notes

Reaction equation

HRID 1467655 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+I)+.

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-7c3fc46a633740deb76e9e2c2d11b6f7
Source dataset
uspto-grants-2015_04
Patent number
US08999987B2

Reaction notes

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