Dicyclohexylcarbodiimide → Ethyl β-oxo-3-pyridinepentanoate

Participants

Reaction Steps

To a mixture of 3-(3-pyridyl)propionic acid (13.6 g, 0.09 mol), Meldrum's acid (13.0 g, 0.09 mol) and dimethylaminopyridine (11 g, 0.09 mol) was added 1,3-dicyclohexylcarbodiimide (18.54 g, 0.09 mol) and DCM (140 ml). The reaction was stirred for 4 h, filtered, concentrated, diluted with 200 ml ethanol and 25 ml 4M HCl/dioxane. The mixture was warmed to reflux 2 h, concentrated, combined with excess sodium carbonate, followed by 50% sodium hydroxide, then triturated with ethyl acetate, filtered, dried (Na2SO4), filtered, then concentrated to give A as an amber oil (19.8 g, 100%). LCMS m/z 222 (MH+)

Provenance & Evidence