Benzene → Ethyl 1-methyl-5-p-toluoylpyrrole-2-acetate

HRID 1605271Notes

Reaction equation

HRID 1605271 reaction equation
[C:1]1([CH3:9])[CH:6]=[CH:5][C:4]([Mg]Br)=[CH:3][CH:2]=1.C1C=CC=CC=1.Cl[C:17]([C:19]1[N:23]([CH3:24])[C:22]([CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:21][CH:20]=1)=[O:18].Cl>CCOCC.[Cl-].[Cd+2].[Cl-]>[CH3:24][N:23]1[C:19]([C:17]([C:4]2[CH:5]=[CH:6][C:1]([CH3:9])=[CH:2][CH:3]=2)=[O:18])=[CH:20][CH:21]=[C:22]1[CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

7

Reactant 4

HCID 241Benzene2×HCID 313Hydrochloric AcidHCID 21546755Ethyl 5-chlorocarbonyl-1-methylpyrrole-2-acetateHCID 178418370HCID 178418370, compound

Product 1

HCID 11011549Ethyl 1-methyl-5-p-toluoylpyrrole-2-acetate

Reagents, catalysts & solvents 2

HCID 24633Cadmium chloride, dihydrateCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a solution of 0.0516 mole of p-tolyl magnesium bromide in ether (40 ml.) is added 5.0 g. (0.0274 mole) of cadmium chloride. The mixture is refluxed for 20 minutes, 50 ml. of dry benzene is added and the ether is distilled off. To this solution of di-(p-tolyl) cadmium is added dropwise 5.9 g. (0.0258 mole) of ethyl 5-chlorocarbonyl-1-methylpyrrole-2-acetate in 25 ml. of benzene. The mixture is stirred at room temperature for 1 hour and poured into dilute HCl. The mixture is extracted with ether. The ether extract is washed successively with dimethylaminopropylamine solution, dilute HCl. and brine and then dried (anhydrous MgSO4). The solvent is evaporated in vacuo. The residue is crystallized from methyl cyclohexane and recrystallized from ethanol to give white crystalline ethyl 1-methyl-5-p-toluoylpyrrole-2-acetate, m.p. 70°-71°C.

Workup

  1. temperatureThe mixture is refluxed for 20 minutes
  2. distillationthe ether is distilled off
  3. additionTo this solution of di-(p-tolyl) cadmium is added dropwise 5.9 g
  4. extractionThe mixture is extracted with ether
  5. extractionThe ether extract
  6. washis washed successively with dimethylaminopropylamine solution, dilute HCl
  7. dry with materialand brine and then dried (anhydrous MgSO4)
  8. customThe solvent is evaporated in vacuo
  9. customThe residue is crystallized from methyl cyclohexane
  10. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-353e5e5b408149dd907a4f477c6bfe5e
Source dataset
uspto-grants-1976_04
Patent number
US03950355

Reaction notes

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