Acetic Acid → 5H-Pyrrolo[1,2-a]imidazol-7-ol,6,7-dihydro-(9CI)

Participants

Reaction Steps

To a solution of imidazole (2 mL, 30.26 mmol) and acetic acid (0.12 mL, 2.12 mmol) in dry dioxane (20 mL) under N2 was added acrolein (3.03 mL, 45.39 mmol) in 1 portion and the resultant solution heated to reflux for 4 hr. The reaction mixture was concentrated in vacuo and the yellow-brown residue was purified by column chromatography, (elution with 25% methanol in DCM) to give the title product; 1H NMR (500 MHz, DMSO) delta 2.25 (1H, ddt, J=13.06, 7.90, 3.94, 3.94 Hz), 2.70-2.87 (1H, m), 3.85 (1H, ddd, J=10.72, 8.51, 4.26 Hz), 4.03 (1H, ddd, J=10.72, 7.80, 6.23 Hz), 4.86 (1H, dd, J=7.09, 3.00 Hz), 5.58 (1H, br. s.), 6.94 (1H, s), 7.06 (1H, d, J=0.95 Hz); LC-MS: m/z=+124.9 (M+H)+.

Provenance & Evidence