4-Ethoxyaniline → 1-(4-Ethoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole

HRID 2375430Notes

Reaction equation

HRID 2375430 reaction equation
[C:1]1([C:7](=O)[CH2:8][CH2:9][C:10](=O)[CH3:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:14][CH2:15][O:16][C:17]1[CH:18]=[CH:19][C:20]([NH2:23])=[CH:21][CH:22]=1>C(O)(=O)C.C1(C)C=CC=CC=1>[CH2:15]([O:16][C:17]1[CH:18]=[CH:19][C:20]([N:23]2[C:10]([CH3:11])=[CH:9][CH:8]=[C:7]2[C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)=[CH:21][CH:22]=1)[CH3:14]

Participants

5

Reactant 2

HCID 90764-EthoxyanilineHCID 1363711-Phenyl-1,4-pentanedione

Product 1

HCID 692752731-(4-Ethoxyphenyl)-2-methyl-5-phenyl-1H-pyrrole

Reagents, catalysts & solvents 2

HCID 176Acetic AcidCatalystHCID 1140TolueneSolvent

Procedure

To a solution of 1-phenyl-1,4-pentanedione (1.06g, 6.0 mmol) and toluene (50 mL) was added p-phenetidine (0.78 mL, 6.0 mmol) and 5 drops of glacial acetic acid. The mixture was heated at reflux overnight. After cooling to rt, the mixture was concentrated in vacuo and purified by flash chromatography on silica gel (15-25% EtOAc/hexanes) to give 1-(p-ethoxyphenyl)-5-methyl-2-phenyl-pyrrole as a yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.17-7.13 (m, 2H), 7.10-7.05 (m, 5H), 6.89-6.84 (m, 2H), 6.35 (d, 1H), 6.08 (d, 1H), 4.04 (q, 2H), 2.13 (s, 3H), 1.44 (t, 3H); MS (ESI) 278 (M+H)+.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux overnight
  3. concentrationthe mixture was concentrated in vacuo
  4. custompurified by flash chromatography on silica gel (15-25% EtOAc/hexanes)

Sources & evidence

ORD record
ord-e34a9698cd2c446bad785ea3a04b0ff3
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

Loading…