Diethyl Oxalate → Ethyl 2-oxo-2-(quinolin-6-yl)acetate

Participants

Reaction Conditions

Reaction Steps

Under inert atmosphere 255 g 6-iodoquinoline (1 mol) is dissolved in THF and cooled to −20° C. and 808 g IpMgCl.LiCl (1.1 moles) is added. This cold solution is added to a solution of 438 g diethyloxalate (3 moles) in 1800 mL THF at low temperature (−78° C.). The reaction mixture is heated to 0° C. and is quenched with a saturated ammonium acetate solution (0.8 L/mole). Ethyl oxo(quinolin-6-yl)acetate is extracted with ethyl acetate (1 L) from this mixture. After chromatography (silica, heptanes/ethyl acetate) ethyl oxo(quinolin-6-yl)acetate was obtained in 70% yield.

Provenance & Evidence