p-Toluenesulfonic acid monohydrate → 2-(4-Benzyloxyphenyl)-5-methyl-1-(4-pentylphenylpropyl)-1H-pyrrole

HRID 1072717Notes

Reaction equation

HRID 1072717 reaction equation
[CH2:1]([C:6]1[CH:11]=[CH:10][C:9]([CH2:12][CH2:13][CH2:14][NH2:15])=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH2:4][CH3:5].[CH2:16]([O:23][C:24]1[CH:29]=[CH:28][C:27]([C:30](=O)[CH2:31][CH2:32][C:33](=O)[CH3:34])=[CH:26][CH:25]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH2:16]([O:23][C:24]1[CH:25]=[CH:26][C:27]([C:30]2[N:15]([CH2:14][CH2:13][CH2:12][C:9]3[CH:8]=[CH:7][C:6]([CH2:1][CH2:2][CH2:3][CH2:4][CH3:5])=[CH:11][CH:10]=3)[C:33]([CH3:34])=[CH:32][CH:31]=2)=[CH:28][CH:29]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 223875251-(4-Benzyloxyphenyl)-1,4-pentanedioneHCID 223875943-(4-Pentylphenyl)propylamine

Product 1

HCID 697319892-(4-Benzyloxyphenyl)-5-methyl-1-(4-pentylphenylpropyl)-1H-pyrroleYield 75%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 3-(4-pentylphenyl)propylamine (1.8 g, 8.8 mmol) and 1-(4-benzyloxyphenyl)-1,4-pentanedione (2.43 g, 8.7 mmol) and p-toluenesulfonic acid monohydrate (200 mg) in toluene (30 ml) was refluxed for 12 hours under heating and the solvent was removed under reduced pressure. The residue was silica gel chromatography (hexane:ethyl acetate=9:1) to give the object compound as an oily substance. 2.99 g, (yield 75%)

Workup

  1. temperatureunder heating
  2. customthe solvent was removed under reduced pressure
  3. customto give the object compound as an oily substance

Sources & evidence

ORD record
ord-c144258e8dda474c9e606f86eae67055
Source dataset
uspto-grants-2005_06
Patent number
US06911468B2

Reaction notes

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