Ammonium Chloride → HCID 68438168, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 4-bromophenethyl alcohol (0.21 g) in tetrahydrofuran (20 mL) was added tert-butyllithium (1.6 mol/L pentane solution, 1.5 mL) at −78° C. under an argon atmosphere, and the mixture was stirred for 30 minutes. To the reaction mixture was added a solution of 3-benzyloxy-4-formyl-5-methyl-1-phenyl-1H-pyrazole (0.10 g) in tetrahydrofuran (3 mL), and the mixture was warmed to 0° C. and stirred for 30 minutes. The reaction mixture was poured into a saturated aqueous ammonium chloride solution, and the mixture was extracted with diethyl ether. The organic layer was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: hexane/ethyl acetate=1/1-1/2) to give an oily substance. The obtained oily substance was dissolved in methanol (4 mL). To the solution was added 10% palladium-carbon powder (0.044 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 17 hours. Insoluble materials were removed by filtration, and the solvent of the filtrate was removed under reduced pressure. Diethyl ether was added to the residue, and the resulting precipitates were collected by filtration and dried under reduced pressure to give the title compound (0.032 g).

Provenance & Evidence