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

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Reaction Steps

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.

Provenance & Evidence