{1-benzyl-3-[(3-([2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzyl)oxy]-1H-pyrazol-4-yl}methanol → 1-benzyl-3-[(3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzyl)oxy]-1H-pyrazole-4-carbaldehyde

HRID 2221748Notes

Reaction equation

HRID 2221748 reaction equation
[CH2:1]([N:8]1[CH:12]=[C:11]([CH2:13][OH:14])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][C:27]3[N:28]=[C:29]([C:33]4[O:34][CH:35]=[CH:36][CH:37]=4)[O:30][C:31]=3[CH3:32])[CH:18]=2)=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH2:1]([N:8]1[CH:12]=[C:11]([CH:13]=[O:14])[C:10]([O:15][CH2:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[C:19]([O:25][CH2:26][C:27]3[N:28]=[C:29]([C:33]4[O:34][CH:35]=[CH:36][CH:37]=4)[O:30][C:31]=3[CH3:32])[CH:18]=2)=[N:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 69216951{1-benzyl-3-[(3-([2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzyl)oxy]-1H-pyrazol-4-yl}methanol

Product 1

HCID 866057661-benzyl-3-[(3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzyl)oxy]-1H-pyrazole-4-carbaldehydeYield 90.4%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of {1-benzyl-3-[(3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzyl)oxy]-1H-pyrazol-4-yl}methanol (0.60 g), activated manganese dioxide (2.0 g) and tetrahydrofuran (50 mL) was stirred at room temperature for 15 hrs. Manganese dioxide was removed by filtration and the filtrate was concentrated. The obtained crystals were collected by filtration to give 1-benzyl-3-[(3-{[2-(2-furyl)-5-methyl-1,3-oxazol-4-yl]methoxy}-4-methoxybenzyl)oxy]-1H-pyrazole-4-carbaldehyde (0.54 g, yield 90%). Recrystallization from ethyl acetate-hexane gave colorless prism crystals. melting point: 142-143° 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-03810c1d049c444990b1d46c9677b6a6
Source dataset
uspto-grants-2008_05
Patent number
US07368578B2

Reaction notes

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