Imidazole → Methyl 1H-imidazol-1-ylacetate

Participants

Reaction Steps

Under nitrogen, combined 1.0 g of imidazole (14.7 mmol) with 824 mg of potassium hydroxide (14.7 mmol), 2.0 g of potassium carbonate (14.7 mmol) and 82 mg of benzyltriethylammonium chloride (7.34 mmol) in 40 ml of CH2Cl2. Added 695 μl of methylbromoacetate. Reaction is stirred at room temperature for 3 hours. Filtered off solids, rinsed with CH2Cl2, and evaporated the filtrate under reduced pressure to give colorless oil. Product is purified by flash chromatography on a Biotage Flash 40 (Eluent: 95:5 CH2Cl2/CH3OH), yielding 300 mg of a white solid (27%). 1H NMR (400 MHz, CD3OD) δ 3.75 (3H, s), 4.91 (2H, s), 6.96 (1H, s), 7.10 (1H, s), 7.64 (1H, s).

Provenance & Evidence