Water → HCID 131716802, compound

Participants

Reaction Conditions

Reaction Steps

Sodium hydride (0.58 g of a 50% dispersion, 12 mmol) was washed twice with hexane and covered with DMF (45 mL). 3,3,5-Triphenyl-3H-pyrazole (3 g, 10 mmol) was added and the mixture heated at 110° C. under nitrogen for 45 minutes before being cooled to room temperature. A solution of ethyl 8-bromo-octanoate (2.80 g, 11 mmol) in DMF (2 mL) was added and the mixture stirred for 10 minutes before being poured onto a mixture of water and ethyl acetate. The aqueous layer was discarded and the organic layer washed twice with water and once with saturated sodium chloride solution. The organic phase was dried over sodium sulfate and concentrated to afford an oil. Chromatography on a column of silica gel using a mixture of hexane and ethyl acetate (17:3) as eluent gave ethyl 3,4,5-triphenyl-1H-pyrazol-1-octanoate hemihydrate (4.05 g, 85%) as an oil. MS(CI): m/e=467 (MH+).

Provenance & Evidence