Trifluoroacetic acid → Methyl 3-phenyl-1H-pyrrole-2-carboxylate

Participants

Reaction Conditions

Reaction Steps

1-tert-Butyl 2-methyl 3-phenyl-1H-pyrrole-1,2-dicarboxylate (18.0 g, 59.7 mmol) was dissolved in CH2Cl2 (20 mL) and cooled to 0° C. TFA (23.0 mL, 0.299 mmol) was added to the reaction mixture and the solution stirred at room temperature for 14 h. The reaction mixture was concentrated under reduced pressure to remove excess of TFA. To the resulting residue was added 10% sodium bicarbonate solution (50 mL) and the aqueous portion extracted with CH2Cl2. The organic layer was separated, dried over sodium sulfate, filtered and concentrated under reduced pressure. The residue was purified by column chromatography using CombiFlash (REDISEP®, silica gel, 40 g, 30% EtOAc/hexanes) to obtain methyl 3-phenyl-1H-pyrrole-2-carboxylate (7.50 g, 62.4%). 1H NMR (400 MHz, DMSO-d6) δ ppm 3.69 (s, 3H), 6.29 (t, J=2.8 Hz, 1H), 7.02 (d, J=2.8 Hz, 1H), 7.03 (m, 5H), 12.0 (s, 1H).

Provenance & Evidence