Dimethyl malonate → HCID 86637416, compound

Participants

Reaction Steps

Dimethyl malonate (4.69 g, 35.5 mmol) was dissolved in DMSO (24.0 ml). This solution was added 70% NaH (1.33 g, 33.2 mmol) at 0° C. The resulting mixture was warmed up to room temperature, then stirred at the same temperature for 40 min. To this solution was added 1-(5,6-dichloropyridin-3-yl)ethanone (Tetrahedron 1992, 48, 9233-9236, 4.50 g, 23.7 mmol) at room temperature, then the resulting mixture was stirred at 100° C. for 4 hours. The mixture was partitioned between Et2O and water. The organic layer was washed with water and brine, dried over Na2SO4, then concentrated to give a brown syrup. The crude material was purified by SiO2 column chromatography (100 g, EtOAc/hexane (1/2)) to give the title compound (2.18 g, 32%) as a yellow oil. 1H NMR (300 MHz, CDCl3) δ 2.64 (3H, s), 3.83 (6H, s), 5.31 (1H, s), 8.26 (1H, s), 9.02 (1H, s).

Provenance & Evidence