(2,6-Dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol → (2,6-Dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

HRID 928811Notes

Reaction equation

HRID 928811 reaction equation
[CH3:1][C:2]1[C:7]([CH:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][CH:11]=2)[OH:9])=[CH:6][CH:5]=[C:4]([CH3:16])[N:3]=1>O1CCOCC1.[O-2].[O-2].[Mn+4]>[CH3:1][C:2]1[C:7]([C:8]([C:10]2[N:14]([CH3:15])[N:13]=[N:12][CH:11]=2)=[O:9])=[CH:6][CH:5]=[C:4]([CH3:16])[N:3]=1

Participants

4

Reactant 1

HCID 86715641(2,6-Dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol

Product 1

HCID 86715642(2,6-Dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanone

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
40 °C

Procedure

A mixture containing (2,6-dimethylpyridin-3-yl)(1-methyl-1H-1,2,3-triazol-5-yl)methanol (9.8 g, 44.9 mmol, Intermediate 54: step a) and manganese dioxide (18.8 g, 184 mmol) in dry dioxane (225 mL) was heated to 100° C. with stirring. After 1 h, the mixture was cooled to 40° C. The cooled mixture was filtered through a 2 cm pad of Celite rinsing with tetrahydrofuran (100 mL). The filtrate was concentrated to provide the title compound as an off-white solid.

Workup

  1. filtrationThe cooled mixture was filtered through a 2 cm pad of Celite
  2. washrinsing with tetrahydrofuran (100 mL)
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-3c47a8a9e53847fb910d2a7693e4162c
Source dataset
uspto-grants-2016_03
Patent number
US09290476B2

Reaction notes

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