Sodium hydride → Methyl (E)-3-(2-quinolinyl)-2-propenoate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(diethoxyphosphoryl)acetate (4.41 g, 20.9 mmol) in THF (8 mL) was added NaH (0.91 g, 22 mmol) and the resultant solution was stirred for 20 min. The reaction mixture was cooled to 0° C. and quinoline-2-carbaldehyde (3.0 g, 19 mmol) in THF (4 mL) was added via syringe. The reaction was allowed to warm to room temperature and stirred for 3 h. The reaction was quenched with saturated sodium bicarbonate (10 mL) and the resulting mixture was extracted with DCM (100 mL). The DCM layer was dried over Na2SO4, filtered, and concentrated in vacuo. The residue obtained was purified by flash column chromatography on silica gel (0-30% EtOAc-heptane) to afford compound 79a. Mass spectrum (LCMS, ESI pos.) Calcd. For C13H11NO2 214.1 (M+H). found 214.1.

Provenance & Evidence