Water → HCID 11449145, compound

Participants

Reaction Conditions

Reaction Steps

Methyl (7-methoxy-2-(2-propenyl)benzofuran-3-yl)acetate (464 mg) was dissolved in dichloromethane (4 ml) and the solution was cooled to 0° C. To this solution, boron tribromide (1.0 M, 3.9 ml) was added and the solution was stirred for 2 hours. Saturated aqueous sodium hydrogen carbonate solution was added to the reaction solution and the resulting solution was poured into water layer (50 ml), followed by extracting the resultant twice with ethyl acetate (30 ml). The organic layers were combined and washed with saturated brine, followed by drying over sodium sulfate. After removing sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was dissolved in THF (15 ml). This solution was cooled to 0° C. and lithium aluminum hydride (91 mg) was added, followed by stirring the resulting mixture at 0° C. for 30 minutes and then at room temperature for 1.5 hours. Ethyl acetate was added to the reaction solution to quench the lithium aluminum hydride, and water (0.2 ml) and acetic acid (0.5 ml) were added, followed by stirring the solution at room temperature for 30 minutes. To this solution, sodium hydrogen carbonate (600 mg) and magnesium sulfate were added and the solution was filtered through Celite. After removing the solvent under reduced pressure, the residue was dissolved in DMF (5 ml). To this solution, methyl bromoacetate (0.5 ml) and potassium carbonate (606 mg) were added and the solution was stirred at room temperature for 17 hours. The reaction solution was poured into water (80 ml) and the resultant was extracted twice with ethyl acetate (20 ml). The organic layers were combined and washed with saturate brine, followed by drying the resultant over sodium sulfate. After removing the sodium sulfate by filtration, the solvent was removed under reduced pressure and the residue was purified by column chromatography (solvent: hexane/ethyl acetate=1/1) using silica gel to obtain the desired compound (450 mg, yield: 87%).

Provenance & Evidence