Tetrahydrofuran → 1-N-Propylphthalimido-1H-pyrrole-3,4-dicarboxylate diethyl ester

Participants

Reaction Conditions

Reaction Steps

A solution of diethyl pyrrole-3,4-dicarboxylate (39 g, 0.185 mol) in THF (1600 mL) was treated with NaH (60%, 7.6 g, 0.19 mol). The reaction mixture was heated to reflux for 1 hour. The reaction was then cooled to 30° C. and N-(3-bromopropyl)phthalimide (52 g, 0.19 mol) was added. The reaction mixture was heated to reflux for 1 hour, cooled, filtered, and concentrated in vacuo. The resultant gum was partitioned between ETOAC/H2O and extracted with EtOAC (2×300 mL). The organic layer was dried (MgSO4), filtered and concentrated in vacuo. The resultant solid was recrystallized from EtOAC to give the title compound 68 g (92%) (mp 100-101° C). 1H NMR (DMSO) δ 1.24 (t, 3H, CH), 2.06 (m, 2H, CH3), 3.57 (t, 2H, CH2), 4.14 (m, 4H, CH2), 7.49 (s, 2H, ArH), 7.86 (m, 4H, ArH).

Provenance & Evidence