Sodium Chloride → 4-Methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester

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Reaction Steps

Sodium hydride (470 mg, 60% in mineral oil, 11.8 mmol) was added to a solution of 4-methyl-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.42 g, 5.84 mmol) in THF (10 mL) at 0° C. and under nitrogen as inert gas and the reaction mixture was stirred for 15 min. Then p-bromobenzyl bromide (2.16 g, 11.7 mmol) was added to the reaction mixture and the reaction mixture was stirred for 30 min at 0° C. and overnight at RT. After the addition of a few drops of water and aq. sat. NaCl solution (100 mL), extraction was performed with DCM (2×50 mL). After drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification was performed via column chromatography. 4-Methyl-1-(4-methylbenzyl)-3-p-tolyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.03 g, 51% of theoretical) was obtained.

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