Dimethylformamide → HCID 19982274, compound

Participants

Reaction Steps

Sodium hydride (1.57 g of 50% dispersion, 32 mmol) was washed twice with hexanes, covered with DMF (100 mL), and a mixture of 3,4-diphenyl-1H-pyrazole and 4,5-diphenyl-1H-pyrazole (6.00 g, 27 mmol) was added. After gas evolution had ceased, the mixture was stirred for 10 minutes before adding methyl 8-bromooctanoate (7.10 g, 30 mmol). The mixture was stirred at room temperature for 40 minutes, diluted with water, and extracted with diethyl ether (3 times). The combined extracts were washed with water (3 times), dried over sodium sulfate, and concentrated in vacuo to leave an oil. Repeated chromatography on a column of silica gel using a mixture of hexanes and diethyl ether (2:1) as eluant provided methyl 3,4-diphenyl-1H-pyrazole-1-octanoate (6.11 g, 59%) as an oil. MS(CI): m/e=377 (MH+).

Provenance & Evidence