Pyrazole → 1-(4-Octylphenoxy)-3-(pyrazol-1-yl)propan-2-ol

Participants

Reaction Steps

0.091 g (3.96 mmol) sodium is mixed with 5 ml absolute THF and with a solution of 0.268 g (3.94 mmol) pyrazole in 15 absolute THF. Having stirred at room temperature for 2 hours, a solution of 0.690 g (2.63 mmol) 2-(4-octylphenoxymethyl)oxirane in 10 ml THF is added drop-wise and boiled under reflux for 8 hours. The cooled reaction mixture is poured into semi-saturated NaCl solution and extracted four times using diethyl ether. The combined organic phases are concentrated to half the volume on the rotary evaporator. Washing using a semi-saturated NaCl solution, drying on sodium sulfate, filtration and reconcentration on the rotary evaporator leave as a crude product a yellow solid which is purified on silica gel by means of column chromatography (flow agent: petroleum ether/ethyl acetate 85:15) and recrystallized from petroleum ether and yields the product as a white solid.

Provenance & Evidence