Water → 2-[Hydroxy(4-methoxyphenyl)methylidene]-5-(propan-2-yl)thiophen-3(2H)-one

Participants

Reaction Conditions

Reaction Steps

1.00 g of (3-benzyloxy-5-isopropyl-thiophen-2-yl)-(4-methoxy-phenyl)-methanone was dissolved in 20 ml of dichloromethane. 2.73 ml of a 1 molar solution of boron tribromide-dimethyl sulfide complex in dichloromethane were added to the reaction solution. The solution was stirred at 22° C. for 1.5 h. The reaction mixture was poured into 50 ml of water, and the mixture was extracted twice with 30 ml of dichloromethane each time. The combined organic phase was extracted twice with 30 ml of saturated sodium bicarbonate solution each time and washed one with 50 ml of saturated sodium chloride solution, dried over sodium sulfate and concentrated. The crude product was purified by column chromatography (SiO2, ethyl acetate/n-heptane=1:4).

Provenance & Evidence