HCID 69423999, compound → HCID 23025073, compound

HRID 350003Notes

Reaction equation

HRID 350003 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[C:19]([CH2:20][OH:21])=[CH:18][N:17]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:25][CH:24]=2)[N: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[C:19]([CH:20]=[O:21])=[CH:18][N:17]([CH2:22][C:23]2[CH:24]=[CH:25][C:26]([O:29][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)=[CH:27][CH:28]=2)[N:16]=1

Participants

4

Reactant 1

HCID 69423999HCID 69423999, compound

Product 1

HCID 23025073HCID 23025073, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-1-(4-phenoxybenzyl)-1H-pyrazol-4-yl]methanol (2.85 g), active manganese dioxide (8.42 g) and tetrahydrofuran (50 ml) was stirred at room temperature overnight. After the manganese dioxide was separated by filtration, the filtrate was concentrated. The residue was subjected to silica gel column chromatography to obtain 3-(5-methyl-2-phenyl-4-oxazolylmethoxy)-1-(4-phenoxybenzyl)-1H-pyrazole-4-carbaldehyde (2.61 g, yield 92%) as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:1, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 129–130° C.

Workup

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

Sources & evidence

ORD record
ord-a7c57b6299594ceba663bf31c09a49fd
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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