Tetrahydrofuran → Methyl (E)-3-(2-quinolinyl)-2-propenoate

Participants

Reaction Steps

To a solution of 2-quinolinecarboxaldehyde (10 g, 64 mmol) in 200 mL THF was added trimethylphosphonoacetate (11.0 mL, 76 mmol) and then sodium hydride (3.05 g of a 60% suspension in oil, 76 mmol). After stirring for 3 h at room temperature, the reaction was quenched by the addition of a saturated ammonium chloride solution. The mixture was extracted twice with EtOAc, the combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was suspended in ˜75 mL Et2O and to that was added ˜125 mL hexanes and the mixture was placed in the freezer. The solids were collected by filtration to provide 8.46 g (62%) of G5 as a pale orange solid. MS (Electrospray): m/z 214.3 (MH+).

Provenance & Evidence