HCID 69423031, compound → HCID 86760415, compound

HRID 349898Notes

Reaction equation

HRID 349898 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:34]=[CH:33][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:22]([CH2:31][OH:32])=[CH: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:16]=[CH:17][C:18]([CH2:19][N:20]2[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][N:26]=3)[C:22]([CH:31]=[O:32])=[CH:21]2)=[CH:33][CH:34]=1

Participants

4

Reactant 1

HCID 69423031HCID 69423031, compound

Product 1

HCID 86760415HCID 86760415, compoundYield 85.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-[4-(5-methyl-2-phenyl-4-oxazolylmethoxy)benzyl]-4-(2-pyridyl)-3-pyrrolyl]methanol (2.01 g), activated manganese dioxide (5.09 g), and tetrahydrofuran (50 ml) was stirred at room temperature overnight. 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]-4-(2-pyridyl)pyrrole-3-carbaldehyde (1.71 g, yield: 85%) was obtained as an oily substance from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

Workup

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

Sources & evidence

ORD record
ord-7fd3d83367884f37af9691d9ec6f2d5b
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

Loading…