[3-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazol-4-yl]methanol → 3-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 2221779Notes

Reaction equation

HRID 2221779 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:44]=[CH:43][C:18]2[C:19]([C:37]3[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=3)=[C:20]([CH2:22][O:23][C:24]3[C:28]([CH2:29][OH:30])=[CH:27][N:26]([C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)[N:25]=3)[O:21][C:17]=2[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:44]=[CH:43][C:18]2[C:19]([C:37]3[CH:38]=[CH:39][CH:40]=[CH:41][CH:42]=3)=[C:20]([CH2:22][O:23][C:24]3[C:28]([CH:29]=[O:30])=[CH:27][N:26]([C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)[N:25]=3)[O:21][C:17]=2[CH:16]=1

Participants

4

Reactant 1

HCID 69215881[3-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazol-4-yl]methanol

Product 1

HCID 866057733-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazole-4-carbaldehydeYield 86.7%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [3-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazol-4-yl]methanol (0.22 g), activated manganese dioxide (0.75 g) and tetrahydrofuran (10 mL) was stirred at room temperature for 3 hrs. Manganese dioxide was removed by filtration and the filtrate was concentrated. The obtained crystals were collected by filtration to give 3-({6-[(5-methyl-2-phenyl-1,3-oxazol-4-yl)methoxy]-3-phenyl-1-benzofuran-2-yl}methoxy)-1-phenyl-1H-pyrazole-4-carbaldehyde as colorless crystals (0.19 g, yield 86%). Recrystallization from ethyl acetate-hexane gave colorless needle crystals. melting point: 176-177° C.

Workup

  1. customManganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. filtrationThe obtained crystals were collected by filtration

Sources & evidence

ORD record
ord-39dd0c42abc7454ca945eb803d62503b
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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