Sodium hydride → 4-(3-chloro-4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one

Participants

Reaction Steps

To a 0° C. solution of 2-(3-chloro-4-methoxyphenyl)-2-oxo-ethyl 2-(4-(quinolin-2-ylmethoxy)phenyl)acetate (750 mg, 1.58 mmol) in DMF (10 mL) was added NaH (190 mg, 3.95 mmol). The reaction mixture was then stirred at RT for 1 h, quenched with ice and extracted with EtOAc (2×50 mL). The combined organic layers were washed with water, dried over Na2SO4, and concentrated in vacuo to obtain the crude product. The crude material was purified via silica gel column chromatography to afford 4-(3-chloro-4-methoxyphenyl)-3-(4-(quinolin-2-ylmethoxy)phenyl)furan-2(5H)-one (40 mg, 6%) as a solid. 1H NMR (500 MHz, d6-DMSO): δ 8.42-8.38 (m, 1H), 8.16-8.05 (m, 2H), 7.72 (t, J=7.6 Hz, 1H), 7.49-7.39 (m, 2H), 7.66 (d, J=8.2 Hz, 1H), 7.58 (t, J=7.2 Hz, 1H), 7.42-7.36 (m, 1H), 7.29-7.20 (m, 2H), 7.17-7.10 (m, 2H), 5.45 (s, 2H), 5.23 (s, 2H), 3.85 (s, 3H). MS: M+H: m/z=458.1. HPLC: 93%, (Condition-H).

Provenance & Evidence