Isopropyl iodide → Methyl 1-isopropyl-1H-pyrrole-3-carboxylate

Participants

Reaction Steps

NaH (58.1 mmol) was added to a solution of 1H-pyrrole-3-carboxylic acid methyl ester [2703-17-5] (38.8 mmol) in DMF (80 mL) at 0° C. and the mixture was stirred for 1.5 h. 2-Iodo-propane (78 mmol) was added and the mixture was stirred at rt for 4 h. The reaction mixture was quenched with 1N aqueous KHSO4 and extracted with EtOAc (3×). The combined organic layers were washed with brine, dried (Na2SO4) and concentrated. The residue was purified using a RediSep® silica gel column to afford the title compound as an orange-brown oil. tR: 3.80 min (HPLC 1); ESI-MS: tR=0.92 min, [M+H]+ 168 (LC-MS 1); TLC: Rf=0.22 (1:6 EtOAc/heptanes).

Provenance & Evidence