Cesium carbonate → 5-(4-Methoxy-3-(2-(2-((2-methyladamantan-2-yl)oxy)-2-oxoethoxy)-2-oxoethyl)phenyl)-dibenzothiophenium chloride

Participants

Reaction Conditions

Reaction Steps

5-(3-(carboxymethyl)-4-methoxyphenyl)-dibenzothiophenium iodide (15.0 g, 31.5 mmol) was dissolved in DMF (100 mL) and degassed with nitrogen for 30 min, then 2-methyladamantan-2-yl 2-chloroacetate (7.49 g, 31.0 mmol) and cesium carbonate (14.4 g, 44.1 mmol) were added sequentially and the mixture stirred at 25° C. for 6 h. The solution was diluted with water (200 mL), extracted with DCM (2×150 mL), the combined organic layers washed with water (5×150 mL) and concentrated to a viscous oil which was poured onto MTBE (1 L) and vigorously stirred for 1 h. The precipitate was filtered, washed with MTBE (2×250 mL) and dried to afford the title compound (18.2 g, 99%) as a white solid. 1H NMR (300 MHz, (CD3)2SO) δ: 8.51 (d, J=8.1 Hz, 2H), 8.29 (d, J=8.1 Hz, 2H), 7.95 (t, J=7.5 Hz, 2H), 7.70-7.81 (m, 3H), 7.32 (d, J=2.1 Hz, 1H), 7.25 (dd, J=7.5, 2.1 Hz, 1H), 4.56 (s, 2H), 3.82 (s, 3H), 3.65 (s, 2H), 2.10-2.19 (m, 2H), 1.61-1.95 (m, 11H), 1.52 (s, 3H), 1.39-1.50 (m, 2H).

Provenance & Evidence