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

HRID 1606168Notes

Reaction equation

HRID 1606168 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]

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 min. The mixture is heated under reflux for 90 min. 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 min.
  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-ed2783d21ba34cd09327aadeeb34d97b
Source dataset
uspto-grants-1976_04
Patent number
US03952012

Reaction notes

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