1-Chloromethylnaphthalene → Diethyl acetamido[(naphthalen-1-yl)methyl]propanedioate

Participants

Reaction Steps

Sodium (28 mmol; 0.64 g) is introduced into 50 cm3 of absolute ethanol, under inert atmosphere. At 0° C., diethyl 2-acetamidomalonate (28 mmol; 6.08 g) dissolved in 35 cm3 of absolute ethanol is added, followed by dropwise addition, with a syringe, of (1-naphthyl)methyl chloride (28 mmol; 4.1 cm3). The mixture is maintained at reflux until the starting material has disappeared (6 h, then overnight at room temperature and then 2 h at reflux). The reaction medium is poured onto a KHSO4 (0.05M; 240 cm3)/hexane (120 cm3) mixture and stirred vigorously. A white precipitate, which is the expected malonic derivative, is recovered.

Provenance & Evidence