2-Chloroethyl methyl sulfide → Diethyl 5-methyl-1-(2-methylsulfanylethyl)-3-phenyl-pyrrole-2,4-dicarboxylate

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Reaction Steps

Potassium t-butoxide (224 mg, 2.00 mmol) was added to a solution of diethyl 5-methyl-3-phenyl-1H-pyrrole-2,4-dicarboxylate (500 mg, 1.66 mmol) in dry dimethylsulfoxide (10 mL) at 10° C. over 5 min. The reaction mixture was allowed to warm to ambient temperature and stirred for 30 min before cooling again to 10° C. 1-Chloro-2-methylsulfanyl-ethane (200 mg, 1.81 mmol) was added slowly and the reaction mixture then stirred at ambient temperature for 72 h. Saturated aqueous ammonium chloride was added and the mixture extracted with diethyl ether. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated in vacuo to afford the crude product. Purification by flash column chromatography over 100-200 mesh silica gel by eluting with 5%-7% ethyl acetate in petroleum ether afforded diethyl 5-methyl-1-(2-methylsulfanylethyl)-3-phenyl-pyrrole-2,4-dicarboxylate (420 mg, 68%) as a liquid.

Provenance & Evidence