Dimethylformamide → 6'-Hydroxy-2'-methoxycarbonylmethoxy-4-methyldihydrochalcone

Participants

Reaction Steps

To a solution of 2′-benzyloxy-6′-hydroxy-4-methylchalcone (0.69 g) in acetone (10 mL)-N,N-dimethylformamide (10 mL) were added potassium carbonate (0.41 g) and methyl bromoacetate (0.21 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with diethyl ether. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was dissolved in methanol (10 mL). To the solution was added 10% palladium-carbon powder (0.29 g), and the mixture was stirred at room temperature under a hydrogen atmosphere for 5 hours. Dichloromethane was added to the mixture, and the insoluble material was removed by filtration. The filtrate was concentrated under reduced pressure to give the title compound (0.58 g).

Provenance & Evidence