Potassium Carbonate → Diethyl 5,8-bis(2,2,2-trifluoroethoxy)quinoline-6,7-dicarboxylate

Participants

Reaction Steps

A mixture containing diethyl 5,8-dihydroxyquinoline-6,7-dicarboxylate 2 (57.8 g, 189 mmol), 2,2,2-trifluoroethyl trifluoromethanesulfonate (100 g, 2.28 equiv) and K2CO3 (62.7 g, 2.4 equiv) in DMF (300 ml) was heated to 70 C for an hour. This mixture was cooled down to r.t. and added to half-saturated NH4Cl (1.5 L). After acidification with AcOH (60 ml), the product was extracted with toluene twice and once with 50% EtOAc/toluene. The combined organics were dried over Na2SO4 and filtered through a 1.2 L pad of silica to remove the polar material. The silica was washed with 10% EtOAc/toluene. Evaporation of the solvents afforded 84.68 g (95% yield) of pure product 3.

Provenance & Evidence