[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]methanol → 1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenylpyrrole-3-carbaldehyde

HRID 349893Notes

Reaction equation

HRID 349893 reaction equation
[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16][N:17]2[CH:21]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]([CH2:28][OH:29])=[CH:18]2)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH3:1][N:2]([CH2:9][CH2:10][O:11][C:12]1[CH:31]=[CH:30][C:15]([CH2:16][N:17]2[CH:21]=[C:20]([C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[C:19]([CH:28]=[O:29])=[CH:18]2)=[CH:14][CH:13]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

4

Reactant 1

HCID 69427226[1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]methanol

Product 1

HCID 867604141-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenylpyrrole-3-carbaldehydeYield 97%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenyl-3-pyrrolyl]methanol (1.45 g), activated manganese dioxide (4.0 g), and tetrahydrofuran (60 ml) was stirred at room temperature for 3 hours. After the manganese dioxide was removed by filtration, the filtrate was concentrated to obtain 1-[4-[2-[N-methyl-N-(2-pyridyl)amino]ethoxy]benzyl]-4-phenylpyrrole-3-carbaldehyde (1.40 g, yield: 97%) as an oily substance.

Workup

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

Sources & evidence

ORD record
ord-2c2a44366596483094ca864d9ba01413
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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