Diethyl methylmalonate → HCID 59233051, compound

Participants

Reaction Conditions

Reaction Steps

To a mixture of NaH (13.42 g, 336 mmol) in dioxane (800 mL) was added diethyl 2-methylmalonate (42.9 ml, 252 mmol) drop-wise at 0° C. The reaction was stirred at 0° C. for 1 hr and allowed to warm to ambient temperature. 3,6-dichloropyridazine (25 g, 168 mmol) was then added portion-wise at 25° C. The reaction was then stirred at reflux for 1 hr. Solvent was removed via rotary evaporation and the resulting residue was dissolved in EtOAc. The organic solution was washed with saturated NaHCO3 (100 mL) followed by 5% citric acid. The organic layer was then dried with MgSO4, filtered, and concentrated to dryness. The resulting residue was purified via MPLC (Hex:EtOAc, 3:1) to provide the title compound, diethyl 2-(6-chloropyridazin-3-yl)-2-methylmalonate 48A (12 g, 25% yield) as a yellow oil. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.18 (s, 6 H) 1.81 (s, 3H) 4.21 (dd, J=7.07, 2.27 Hz, 4 H) 8.00 (s, 2 H). ESI-MS:m/z 287.1 (M+H)+.

Provenance & Evidence