Acetic Acid → Ethyl 3-ethyl-5-formyl-4-methyl-1H-pyrrole-2-carboxylate

Participants

Reaction Steps

To a solution of ethyl 3-ethyl-4,5-dimethyl-1H-pyrrole-2-carboxylate (Salor-Aldrich) (0.0147 g, 0.077 mmol) in acetic acid (5 mL), THF (4 mL) and water (4 mL) was added ceric ammonium nitrate (0.169 g, 0.31 mmol) and the reaction was stirred at ambient temperature. After 1.5 h, the reaction was poured into water (10 mL) and extracted with CH2Cl2 (3×5 mL). The combined organic layers were washed with saturated NaHCO3, dried over Na2SO4, filtered, and concentrated. The resultant residue was purified by normal phase chromatography. Proton NMR for the product was consistent with the title compound. 1H NMR (500 MHz, CDCl3) δ 9.78 (s, 1H); 4.36 (q, J=7.1 Hz, 2H); 2.76 (q, J=7.6 Hz, 2H); 1.62 (s, 3H); 1.38 (t, J=7.1 Hz, 3H); 1.13 (t, J=7.6 Hz, 3H). HRMS (ES) exact mass calculated for C11H16NO3 (M+H+): 209.1052. Found 209.1050.

Provenance & Evidence