Toluene → HCID 15725739, compound

Participants

Reaction Steps

A mixture of 3,4,5-triphenyl-lH-pyrazol-1-hexanol (5 g, 12 mmol), tert-butyl bromoacetate (4.92 g, 4.10 mL, 25 mmol), tetrabutylammonium hydrogen sulfate (0.4 g), 50% aqueous sodium hydroxide solution (80 mL) and toluene (80 mL) was stirred vigorously at room temperature. After 18 hours, the reaction mixture was diluted with water (100 mL), the organic layer separated and the aqueous layer extracted twice with diethyl ether. The combined extracts were dried over sodium sulfate and the solvent evaporated to give an oil which was chromatographed on a column of silica gel. Elution with a mixture of hexane and diethyl ether (2:1) afforded 1,1-dimethylethyl [[6-(3,4,5-triphenyl-lH-pyrazol-1-yl)hexyl]oxy]acetate (5.84 g, 95%) as an oil that slowly crystallized to a white solid; m.p. =69°-72° C. MS(CI): m/e =511 (MH+).

Provenance & Evidence