Dimethylformamide → methyl 6-oxo-3,4-diphenyl-1(6H)-pyridazinenonanoate

Beteiligte Stoffe

Reaktionsschritte

Sodium hydride (840 mg of a 60% dispersion in oil, 20 mmol) was washed twice with hexanes, covered with DMF (25 mL) and 5,6-diphenyl-3(2H)-pyridazinone (4 g, 16 mmol), obtained according to P. Schmidt, et al., Helvetica Chim. Acta., 37, 134-140 (1954), added. After gas evolution had ceased, the mixture was stirred at room temperature for 30 minutes before adding methyl 9-bromononanoate (4.45 g, 18 mmol). The mixture was heated briefly to 110° C. to give a solution and then allowed to cool before being stirred at room temperature for 1 hour. The mixture was diluted with water and extracted with diethyl ether (3×). The combined extracts were washed with water, dried over sodium sulfate and concentrated to leave an oil. Chromatography on a column of silica gel afforded methyl 6-oxo-3,4-diphenyl-1(6H)-pyridazine nonanoate (6.44 g, 95%) as an oil.

Herkunft & Nachweise