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4-Methylbenzoyl Chloride → Ethyl 1,4-dimethyl-3-ethoxycarbonyl-5-(p-toluoyl)-pyrrole-2-acetate

HRID 1275291
Notes
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Reaction equation

HRID 1275291 reaction equation
[C:1]1([CH3:10])[CH:6]=[CH:5][C:4]([C:7](Cl)=[O:8])=[CH:3][CH:2]=1.[Cl-].[Al+3].[Cl-].[Cl-].[CH2:15]([O:17][C:18]([C:20]1[C:24]([CH3:25])=[CH:23][N:22]([CH3:26])[C:21]=1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29])=[O:19])[CH3:16]>ClCCCl>[CH3:26][N:22]1[C:23]([C:7]([C:4]2[CH:5]=[CH:6][C:1]([CH3:10])=[CH:2][CH:3]=2)=[O:8])=[C:24]([CH3:25])[C:20]([C:18]([O:17][CH2:15][CH3:16])=[O:19])=[C:21]1[CH2:27][C:28]([O:30][CH2:31][CH3:32])=[O:29]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 134054-Methylbenzoyl ChlorideHCID 118460Ethyl 3-(ethoxycarbonyl)-1,4-dimethyl-1H-pyrrole-2-acetateHCID 6451240Aluminum(III) Chloride

Product 1

HCID 18424258Ethyl 1,4-dimethyl-3-ethoxycarbonyl-5-(p-toluoyl)-pyrrole-2-acetate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

A solution of 30.8 g. p-toluoyl chloride and 26.6 g. (0.2 mole) of aluminum chloride in 250 ml. of 1,2-dichloroethane is added to a refluxing solution of 50.6 g. (0.2 mole) of ethyl 3-ethoxycarbonyl-1,4-dimethylpyrrole-2-acetate in 250 ml. of 1,2-dichloroethane over 30 minutes. The mixture is heated under reflux for 90 minutes, and poured into ice-diluted hydrochloric acid. The organic solution is separated, washed with brine, and dried over magnesium sulfate. The solvent is evaporated in vacuo, and the residue is recrystallized from methanol to give ethyl 1,4-dimethyl-3-ethoxycarbonyl-5-(p-toluoyl)-pyrrole-2-acetate as a white solid, m.p. 108-111° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureunder reflux for 90 minutes
  3. additionpoured into ice-diluted hydrochloric acid
  4. customThe organic solution is separated
  5. washwashed with brine
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent is evaporated in vacuo
  8. customthe residue is recrystallized from methanol

Sources & evidence

ORD record
ord-01dbf89ddd594c5e971dbe6ca3bd8a18
Source dataset
uspto-grants-2000_12
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06160003

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes