Iodine → HCID 68441206, compound

Participants

Reaction Steps

A Grignard reagent was prepared from 4-bromoanisole (1.2 g), magnesium (0.16 g), a catalytic amount of iodine and tetrahydrofuran (20 mL) in the usual manner. To the obtained Grignard reagent solution was added a solution of 3-benzyloxy-4-formyl-5-methyl-1-phenyl-1H-pyrazole(1.5 g) in tetrahydrofuran (15 mL) at 0° C., and the mixture was stirred for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (50 mL) and tetrahydrofuran (50 mL). To the solution was added 10% palladium-carbon powder, and the mixture was stirred at room temperature under a hydrogen atmosphere overnight. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. To the residue was added ethanol, and the precipitates was collected by filtration, washed with ethanol and hexane, and dried under reduced pressure to give the title compound (0.78 g).

Provenance & Evidence