[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]methanol → 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carbaldehyde

HRID 349934Notes

Reaction equation

HRID 349934 reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([CH2:25][OH:26])[CH:22]=[N:21]2)=[CH:17][CH:16]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][O:14][C:15]1[CH:28]=[CH:27][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([CH:25]=[O:26])[CH:22]=[N:21]2)=[CH:17][CH:16]=1

Participants

4

Reactant 1

HCID 69422348[1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]methanol

Product 1

HCID 230247841-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carbaldehydeYield 94%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazol-4-yl]methanol (2.82 g), activated manganese dioxide (6.00 g), and tetrahydrofuran (50 ml) was stirred at room temperature for 2 hours. After the manganese dioxide was removed by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography, and 1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-1H-pyrazole-4-carbaldehyde (2.63 g, yield: 94%) was obtained as a colorless oily substance from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio).

Workup

  1. customAfter the manganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated

Sources & evidence

ORD record
ord-c9c354b764d8436082f9732213abc70d
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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