Diethyl Malonate → 2-(7-Fluoro-2-methoxy-quinolin-8-ylmethyl)-malonic acid diethyl ester

Participants

Reaction Conditions

Reaction Steps

To a suspension of NaH (60% dispersion in oil, 0.88 g, 22 mmol) in THF (100 mL), was added diethyl malonate (3.79 g, 23.66 mmol). The reaction mixture was cooled to 0° C. and 8-bromomethyl-7-fluoro-2-methoxy-quinoline (5.4 g, 20 mmol) was added in one portion. The reaction proceeded 30 min at 0° C. and 15 min at rt. The reaction mixture was quenched by adding water (20 mL) and 10% NaHSO4 (100 mL). The two layers were decanted and the aq. layer was extracted once with EA (100 mL). The combined org. layers were washed with brine, dried over Na2SO4, filtered and concentrated to dryness. The residue was purified by CC (Hept-EA 4:1) to afford the title compound as a yellowish oil (6.4 g). The product was contaminated with 20% of diethyl malonate.

Provenance & Evidence