Tetrahydrofuran → 3-{4-[1-Ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxymethyl}-pentan-3-ol

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Reaction Steps

To a mixture of {4-[1-ethyl-1-(6-methoxy-benzo[b]thiophen-2-yl)-propyl]-2-methyl-phenoxy}-acetic acid methyl ester (1.50 g, 3.64 mmol) and THF (20 mL) is added ethyl magnesium bromide (3.0 mL, 9.1 mmol, 3M in THF). The solution is heated at a reflux for 3 h, diluted with saturated ammonia chloride solution (80 mL), extracted with diethyl ether (2×75 mL), dried over MgSO4, filtered, and concentrated. The residue is purified by silica gel chromatography (10% to 30% EtOAc gradient) to give the title compound (0.90 g, 2.04 mmol, 56%). 1H NMR (CDCl3), δ 0.75 (t, J=7.6 Hz, 6H), 0.95 (t, J=7.4 Hz, 6H), 1.68 (q, J=14.8, 7.5 Hz, 4H), 2.13-2.24 (m, 7H), 3.81 (s, 2H), 3.86 (s, 3H), 6.73 (dd, J=8.2 Hz, 1H), 6.89 (dd, J=8.8, 2.6 Hz, 1H), 7.06 (s, 2H), 7.09 (dd, J=8.4, 2.5 Hz, 1H), 7.17 (d, J=2.7 Hz, 1H), 7.55 (d, J=8.8 Hz, 1H). LC/MS (m/z): calcd. for C27H37O3S (M+H)+: 441.3; found: 441.2.

Provenance & Evidence