Ceric ammonium nitrate → 2-formyl-1-isopropyl-1H-pyrrole-3-carboxylic acid ethyl ester

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Reaction Steps

CAN (979 mmol) was added to a mixture of 1-isopropyl-2-methyl-1H-pyrrole-3-carboxylic acid ethyl ester [224180-70-5] (218 mmol) in CH3CN (1800 mL) and water (360 mL) at 15° C. After 10 min, the reaction mixture was quenched with ice and extracted with MTBE. The organic phase was successively washed with a saturated aqueous solution of NaHCO3 (2×) and brine, dried (Na2SO4), filtered and concentrated. The residue was purified by silica gel column chromatography to afford the title compound as a yellow oil. tR: 4.43 min (HPLC 1); ESI-MS: tR=1.06 min, [M+H]+ 210 (LC-MS 1); TLC: Rf=0.21 (1:9 EtOAc/heptanes).

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