[1-(3,5-Dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol → 1-(3,5-Dibenzyloxybenzyl)-4-phenylpyrrole-3-carbaldehyde

HRID 349901Notes

Reaction equation

HRID 349901 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:26]=[C:27]([O:29][CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[CH:28]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH2:24][OH:25])=[CH:14]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH2:30]([O:29][C:27]1[CH:26]=[C:11]([CH:10]=[C:9]([O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:28]=1)[CH2:12][N:13]1[CH:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]([CH:24]=[O:25])=[CH:14]1)[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

4

Reactant 1

HCID 23024986[1-(3,5-Dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol

Product 1

HCID 230250681-(3,5-Dibenzyloxybenzyl)-4-phenylpyrrole-3-carbaldehydeYield 97.5%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-(3,5-dibenzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol (23.8 g), activated manganese dioxide (50.00 g), and tetrahydrofuran (200 ml) was stirred at room temperature for two hours. After the manganese dioxide was removed by filtration, the filtrate was concentrated. The colorless crystals obtained were collected by filtration to yield 1-(3,5-dibenzyloxybenzyl)-4-phenylpyrrole-3-carbaldehyde (23.10 g, yield: 97%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 117–118° C.

Workup

  1. customAfter the manganese dioxide was removed by filtration
  2. concentrationthe filtrate was concentrated
  3. customThe colorless crystals obtained
  4. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-6e398ebc86d647c29c5ca98b1aa5bc2d
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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