Toluene → HCID 14360978, compound

Participants

Reaction Steps

A solution of triethyl-2-phosphonobutyrate (26.6 g, 118.7 mmol) in dry toluen (250 ml) was cooled on ice and added sodium hydride (60% in oil, 3.3 g, 134.6 mmol). After stirring at 0° C. for 20 min. a solution of quinolinecarboxaldehyde (12.5 g, 79.5 mmol) in dry THF (30 mL) was added. The mixture was slowly warmed to room temperature, and stirring continued for 24 h. The reaction mixture was quenched with ethanol and added water. The aqueous phase was extracted with dichloro methane (×2). The combined organic phases were dried (MgSO4), filtered and concentrated in vacuo. The residue was submitted to flash chromatography, eluting with heptane graduated to heptane/ethyl acetate (4:1), to give 12.5 g (70%) of (E)-3-quinolin-2-yl-acrylic acid ethyl ester.

Provenance & Evidence