Potassium Carbonate → 4-[3-[6-(3,5-Dichloro-phenylsulfanyl)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of 3,5-dichlorothiophenol (1.67 g, 9.34 mmol) in MeCN (120 mL) and DMF (80 mL), 4-[3-(6-bromo-hexyl)-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester (4.0 g, 8.49 mmol) was added, followed by K2CO3 (3.52 g, 25.48 mmol). The reaction mixture was stirred at 80° C. overnight. At this time, after cooling, the reaction was diluted with EtOAc (300 mL), washed with water (twice with 150 mL) and brine, and dried over Na2SO4. Concentration under reduced pressure provided an oil. A sample (2.73 g) was purified by FCC (10% EtOAc/Hex) provide a pure sample (1.20 g) of 4-[3-[6-(3,5-Dichloro-phenylsulfanyl)-hexyl]-2-(2-ethoxycarbonyl-ethyl)-phenoxy]-butyric acid ethyl ester. 1H NMR (CDCl3): δ 7.26 (s, 1H), 7.12 (s, 2H), 7.09 (dd, 1H), 6.75 (d, 1H), 6.69 (d, 1H), 4.14 (m, 4H), 3.99 (t, 2H), 2.98-2.89 (m, 4H), 2.64-2.46 (m, 6H), 2.13 (m, 2H), 1.67-1.39 (m, 8H), 1.27 (m, 6H).

Provenance & Evidence