Methyl iodide → ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate

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Reaction Steps

To a solution of 4-methyl-2-pyrrolecarboxylic acid ethyl ester (100 mg, 0.653 mmol) in THF (2.5 mL), was added NaH (31.3 mg, 0.783 mmol). The mixture was stirred for 10 min and then MeI (0.061 mL, 0.979 mmol) was added dropwise. The resulting mixture was stirred overnight. The reaction was quenched with sat. NH4Cl. The aqueous layer was extracted with EtOAc (3×). The combined organic layers were washed with brine (1×), dried (Na2SO4) and concentrated in vacuo. The residue was purified by preparative TLC (1000 μm, hexanes/EtOAc (9:1)) to give ethyl 1,4-dimethyl-1H-pyrrole-2-carboxylate. 1H NMR (500 MHz, CDCl3): δ 6.77 (s, 1H); 6.58 (s, 1H); 4.28 (q, J=7.1 Hz, 2H); 3.88 (s, 3H); 2.08 (s, 3H); 1.35 (t, J=7.1 Hz, 3H).

Provenance & Evidence