Toluene → 2,5-dimethyl-1-(4-ethoxyphenyl)pyrrole

HRID 2375368Notes

Reaction equation

HRID 2375368 reaction equation
[CH2:1]([CH2:5][C:6](=O)[CH3:7])[C:2]([CH3:4])=O.C1(C)C=CC=CC=1.[CH3:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([NH2:25])=[CH:23][CH:24]=1>C(O)(=O)C>[CH3:7][C:6]1[N:25]([C:22]2[CH:23]=[CH:24][C:19]([O:18][CH2:17][CH3:16])=[CH:20][CH:21]=2)[C:2]([CH3:4])=[CH:1][CH:5]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 80352,5-HexanedioneHCID 90764-Ethoxyaniline

Product 1

HCID 8460412,5-dimethyl-1-(4-ethoxyphenyl)pyrrole

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of acetonyl acetone (11.7 mL, 100 mmol) and toluene (750 mL) was added p-phenetidine (12.9 mL, 100 mmol) and glacial acetic acid (1 mL). The mixture was heated at reflux overnight. After cooling to rt, the mixture was concentrated in vacuo and purified by column chromatography on silica gel (15% EtOAc/hexanes) to give 2,5-dimethyl-1-(4-ethoxyphenyl)pyrrole as a pale yellow solid: 1H NMR (CDCl3, 500 MHz) δ 7.13-7.10 (m, 2H), 6.97-6.94 (m, 2H), 5.88 (br s, 2H), 4.08 (q, 2H), 2.02 (s, 6H), 1.46 (t, 3H); MS (ESI) 216 (M+H)+.

Workup

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

Sources & evidence

ORD record
ord-aad921157fae46d5987031026d18e8c8
Source dataset
uspto-grants-2008_12
Patent number
US07465730B2

Reaction notes

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