Imidazole → 1-Phenethylimidazole

Participants

Reaction Steps

Under an atmosphere of N2, a mixture of imidazole (788 mg, 11.57 mmol, 2.1 equiv) and potassium carbonate (370 mg, 2.68 mmol, 1 equiv) in dry THF (18 mL) was stirred at rt for 10 min. To this was added a solution of (2-bromoethyl)benzene (1.00 g, 5.40 mmol, 1 equiv) in THF (1 mL) and the mixture was heated at reflux temperature for 14 h. The mixture was filtered and the filtrate was concentrated to a clear oil. The oil was dissolved in CH2Cl2 and the organic phase was washed with water (2×). The CH2Cl2 layer was then extracted with dilute aqueous HCl (3×). The aqueous extract was then neutralized with solid NaHCO3, and the free base extracted using CH12Cl2 (3×). The combined organic extracts were dried Na2SO4) and concentrated. High-vacuum drying gave QC-207 (420 mg, 2.44 mmol, 45%) as a clear oil: 1H NMR (400 MHz, CDCl3): δ 3.05 (t, J=7.0 Hz, 2H), 4.17 (t, J=7.0 Hz, 2H), 6.83 (s, 1H), 7.01-7.09 (m, 3H), 7.22-7.34 (m, 4H); 13C NMR (100 Adz, CDCl3): δ 38.0, 48.6, 118.9, 127.1, 128.7, 128.9, 129.6, 137.2, 137.6.

Provenance & Evidence