Methyl 9-bromononanoate → HCID 15725722, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (588 mg of a 60% dispersion in mineral oil, 13 mmol) was washed twice with hexane and covered with dimethylformamide (DMF), (45 mL). 3,3,5-Triphenyl-3H-pyrazole (3 g, 10 mmol) was added and the mixture stirred at 110° C. under a nitrogen atmosphere for 30 minutes before being cooled to room temperature. Methyl 9-bromononanoate (2.80 g, 11 mmol) in DMF (2 mL) was added dropwise, the mixture stirred at room temperature for 2 hours and then poured onto water (100 mL). The mixture was extracted with diethyl ether (3×100 mL), the extracts washed with water (3×100 mL), dried over sodium sulfate and concentrated to give an oil. Chromatography on a column of silica gel using a mixture of hexane and diethyl ether (2:1) as eluent afforded methyl 3,4,5-triphenyl-1H-pyrazol-1-nonanoate (4.72 g, 100%) as a viscous oil. (MS(CI): m/e=467 (MH+)

Provenance & Evidence