Water → HCID 15725737, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (1.30 g of 60% dispersion, 32 mmol) was washed twice with hexane and covered with dimethylformamide (DMF) (100 mL). 3,3,5-Triphenyl-3H-pyrazole (8 g, 27 mmol) was added and the mixture stirred at 110° C. uhder an atmosphere of nitrogen for 25 minutes before being cooled to room temperature. Ethyl 6-bromohexanoate (6.6 g, 5.3 mL, 29 mmol) in DMF (2 mL) was added dropwise and the mixture stirred at room temperature. After 15 minutes water was added and the mixture extracted with diethyl ether (4 times). The combined extracts were washed with water (3 times), dried and concentrated in vacuo to give an oil. Chromatography on a column of silica gel using a mixture of hexane and diethyl ether (11:9) as eluent afforded ethyl 3,4,5-triphenyl-1H-pyrazol-1-hexanoate (11.83 g, 100%) as a viscous oil. MS(CI): m/e=439 (MH+)

Provenance & Evidence