Sodium hydride → (E)-3-[7-(1-phenylethoxy)-benzofuran-2-yl]-but-2-enoic acid-diethylamide

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Reaction Steps

While replacing with nitrogen, NaH (0.13 g, 0.0054 mol) was suspended in absolute THF (20 mL), and N,N-diethylphosphonoacetamide (1.36 g, 0.0054 mol)/absolute THF (10 mL) was added dropwise at 0° C. Then, 2-acetyl-7-(1-phenylethoxy)benzo[b]furan (1.0 g, 0.0036 mol)/absolute THF (20 mL) was added dropwise. After stirring for 6 h while allowing to warm to room temperature, the disappearance of the starting materials was confirmed by TLC. The reaction mixture was poured into saturated aqueous NH4Cl solution, mixed and THF was evaporated under reduced pressure. The residue was extracted with ethyl acetate, washed with brine, dried over absolute magnesium sulfate, and evaporated under reduced pressure to give a pale-yellow oil. The obtained oil was purified by column chromatography to give the title compound as a pale-yellow oil. (0.75 g, 55.6%)

Provenance & Evidence