Iodoethane → 6-Ethoxy-1H-indole

Participants

Reaction Steps

Sodium hydride (60% in mineral oil, 1.65 g, 41 mmol) was added to a solution of 6-hydroxyindole (5.0 g, 38 mmol) in anhydrous DMF (25 mL) at −20° C. under N2. The resulting dark green solution was allowed to warm up to room temperature and stirred for 10 min. Ethyl iodide (3.3 mL, 6.4 g, 41 mmol) was added, and the resulting solution was stirred at room temperature for 1 h. The mixture was poured into ice-water (150 mL), and extracted with EtOAc (3×200 mL). The organic solution was dried (MgSO4) and concentrated at reduced pressure. The residue was purified by flash chromatography (SiO2, 5% then 15% EtOAc/hexanes) to give the title compound (4.5 g, 75%) as a white solid. 1H NMR (CDCl3) δ 7.98 (br. s, 1H), 7.50 (m, 1H), 7.10 (m, 1H), 6.90 (m, 1H), 6.80 (m, 1H), 6.45 (m, 1H), 4.10 (q, J=6.5 Hz, 2H), 1.45 (t, J=6.5 Hz, 3H).

Provenance & Evidence