Sodium Chloride → Ethyl 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylate

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Reaction Steps

Sodium hydride (436 mg, 60% in mineral oil, 10.9 mmol) was added to a solution of 4-methyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.25 g, 5.45 mmol) in THF (10 mL) at 0° C. and under nitrogen as inert gas and the reaction mixture was stirred for 15 min. Then methyl iodide (1,547 g, 10.9 mmol) was added to the reaction mixture and the reaction mixture was stirred for 1 h at 0° C. and overnight at RT. After the addition of a few drops of water and aq. sat. NaCl solution (250 mL), extraction was performed with DCM (2×250 mL). After drying of the combined organic phases over sodium sulfate, filtration and removal of the solvent, purification was performed by means of column chromatography. The desired product 1,4-dimethyl-3-phenyl-1H-pyrrole-2-carboxylic acid ethyl ester (1.02 g, 77% of theoretical) was obtained.

Provenance & Evidence