Cesium carbonate → 2-[6-(Benzothiazol-2-yloxy)-benzofuran-3-yl]-ethanol

Participants

Reaction Steps

To a solution of 3-(2-hydroxy-ethyl)-benzofuran-6-ol (0.42 g, 2.4 mmol) in MeCN (10 mL) was added Cs2CO3 (0.77 g, 2.4 mmol) and 2-chlorobenzthiazole (0.29 mL, 2.4 mmol) and the reaction mixture was stirred (rt, 15 h) and then heated (60° C., 2 h). The reaction mixture was cooled (rt) and partitioned with EtOAc and brine (50 mL each). The aqueous layer was extracted with EtOAc (50 mL). The combined organic layers were washed with brine (50 mL), dried, filtered and concentrated in vacuo. The resulting residue was purified by silica gel flash chromatography using EtOAc:hexane (0-100%) to provide the title compound as an amber oil (0.37 g, 50%). MS (ESI): mass calcd. for C17H13NO3S, 311.4; m/z found, 312.1 [M+H]+. 1H NMR (500 MHz, CDCl3): 7.73 (d, J=8.0, 1H), 7.67 (d, J=8.0, 1H), 6.61 (d, J=8.5, 1H), 7.58 (br s, 1H), 7.53 (d, J=2.0, 1H), 7.41-7.37 (m, 1H), 7.29-7.26 (m, 2H), 3.97-3.93 (m, 2H), 3.96 (t, J=6.5, 2H), the hydroxyl proton was not detected.

Provenance & Evidence