Diethyl Oxalate → Ethyl 2,4-dioxo-4-(pyridin-4-yl)butanoate

Participants

Reaction Steps

The title compound was prepared in the same manner as intermediate 29 using sodium metal (0.466 g, 20.26 mmol), 1-(4-pyridinyl)ethanone (1 g, 6.66 mmol), and diethyl ethanedioate (2.388 mL, 17.62 mmol). The crude product was purified using column chromatography (0 to 100% EtOAc/hexanes) to give 0.95 g of product (24%). LCMS E-S (M+H)=222.0. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.37-1.55 (m, 3 H), 4.43 (q, J=7.07 Hz, 2 H), 7.06-7.16 (m, 1 H), 7.72-7.92 (m, 2 H), 8.82-8.94 (m, 2 H).

Provenance & Evidence