Nitrogen → HCID 59637290, compound

Participants

Reaction Steps

NaH (33.08 g (19.85 mol, 60%) was washed with n-hexane, then dry DMF (500 mL) was added drop wise under N2 atmosphere and the mixture was stirred well. A solution of 3-(trifluoromethyl)-1H-pyrazole (75 g, 0.55 mol) in DMF (125 mL) was added drop wise under N2 atmosphere. Then a solution of 4-methoxylbenzyl chloride (86.3 g, 0.55 mol) in DMF (125 mL) was added drop wise and the overall reaction mixture was allowed to stir for 12 h at room temperature. Progress of the reaction was monitored by TLC (10% ethyl acetate/hexane, Rf˜0.4). On completion of the reaction, the reaction contents were poured into ice water (500 mL) and the product was extracted with ethyl acetate (2×400 mL). The ethyl acetate layer was washed with 2N HCl (2×200 ml). Then the contents were dried over sodium sulfate and concentrated under reduced pressure. The obtained crude product was purified by CC with 10% ethyl acetate/n-hexane to yield 1-(4-methoxybenzyl)-3-(trifluoromethyl)-1H-pyrazole as a brown colored liquid (98 g, 70%).

Provenance & Evidence