[1-(4-Benzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol → 1-(4-Benzyloxybenzyl)-4-phenylpyrrole-3-carbaldehyde

HRID 349888Notes

Reaction equation

HRID 349888 reaction equation
[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:16]([CH2:25][OH:26])=[CH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1>[O-2].[O-2].[Mn+4].O1CCCC1>[CH2:1]([O:8][C:9]1[CH:28]=[CH:27][C:12]([CH2:13][N:14]2[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=3)[C:16]([CH:25]=[O:26])=[CH:15]2)=[CH:11][CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23025097[1-(4-Benzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol

Product 1

HCID 230249941-(4-Benzyloxybenzyl)-4-phenylpyrrole-3-carbaldehydeYield 98.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-(4-benzyloxybenzyl)-4-phenyl-3-pyrrolyl]methanol (19.00 g), activated manganese dioxide (41.19 g), and tetrahydrofuran (300 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-benzyloxybenzyl)-4-phenylpyrrole-3-carbaldehyde (18.56 g, yield: 98%) was obtained as colorless crystals from the fraction eluted with ethyl acetate-hexane (1:2, volume ratio). This was recrystallized from ethyl acetate-hexane. Melting point: 100–101° C.

Workup

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

Sources & evidence

ORD record
ord-d7201b723f224f92852c0cbce2e9dcc2
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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