[1-(6-Benzyloxy-2-naphthylmethyl)-4-phenyl-3-pyrrolyl]methanol → 1-(6-Benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carbaldehyde

HRID 349895Notes

Reaction equation

HRID 349895 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][N:20]1[CH:24]=[C:23]([C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[C:22]([CH2:31][OH:32])=[CH:21]1)[CH:13]=[CH:12]2)[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:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([CH2:19][N:20]1[CH:24]=[C:23]([C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)[C:22]([CH:31]=[O:32])=[CH:21]1)[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 1

HCID 23024834[1-(6-Benzyloxy-2-naphthylmethyl)-4-phenyl-3-pyrrolyl]methanol

Product 1

HCID 230248651-(6-Benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carbaldehydeYield 94.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of [1-(6-benzyloxy-2-naphthylmethyl)-4-phenyl-3-pyrrolyl]methanol (2.39 g), activated manganese dioxide (4.80 g), and tetrahydrofuran (50 ml) was stirred at room temperature for one hour. After the manganese dioxide was removed by filtration, the filtrate was concentrated. The colorless crystals obtained were collected by filtration to yield 1-(6-benzyloxy-2-naphthylmethyl)-4-phenylpyrrole-3-carbaldehyde (2.24 g, yield: 94%). This was recrystallized from tetrahydrofuran-hexane. Melting point: 140–141° 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-b8b90a2cbb064e5eb96f2e91ed892994
Source dataset
uspto-grants-2007_02
Patent number
US07179823B1

Reaction notes

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