Potassium Carbonate → Ethyl 3-[4-[[5-[(tert-butyl(dimethyl)silyl)oxymethyl]-4-methoxy-2-thienyl]methoxy]-2-fluoro-phenyl]propanoate

Participants

Reaction Steps

To a solution of 3-(2-fluoro-4-hydroxy-phenyl)-propionic acid ethyl ester (1.03 g, 4.8 mmol) in acetonitrile (15 mL) is added potassium carbonate (2.31 g, 16.8 mmol) and (5-bromomethyl-3-methoxy-thiophen-2-ylmethoxy)-tert-butyl-dimethyl-silane (1.7 g, 4.8 mmol) at room temperature and the reaction mixture is refluxed for 3 hours. The reaction mixture is concentrated, diluted with water, and extracted with EtOAc (2×30 mL). The combined extracts are washed with water (15 mL) and saturated brine (15 mL), dried over Na2SO4, filtered, and concentrated. The crude material is purified by silica gel chromatography eluting with hexane:ethyl acetate (9.6:0.4) to give the title compound (0.5 g, 21%). 1H NMR (400 MHz, DMSO d6) δ 7.51 (s, 1H), 7.26-7.2 (t, J=8.4 Hz, 1H), 6.92-6.89 (d, J=12 Hz, 1H), 6.83-6.81 (d, J=7.6 Hz, 2H), 4.92 (s, 2H), 4.82 (s, 2H), 4.10-4.05 (q, J=6.4 Hz, 2H), 3.82 (s, 3H), 2.86-2.82 (t, J=16 Hz, 2H), 2.61-2.55 (m, 2H), 1.21-1.17 (t, J=6.8 Hz, 3H), 0.89 (s, 9H), 0.13 (s, 6H).

Provenance & Evidence