Hydrogen Peroxide → HCID 11356211, compound

Participants

Reaction Conditions

Reaction Steps

3-(2-propenyl)-7-methoxybenzofuran (2.19 g) was dissolved in anhydrous tetrahydrofuran (25 ml) under argon atmosphere and the solution was cooled to 0° C. Borane dimethylsulfide complex (2M solution in THF, 6.1 ml) was added and the solution was stirred at room temperature for 2 hours. The reaction solution was cooled to 0° C. and ethanol (20 ml), 3N aqueous sodium hydroxide solution (1.3 ml) and 30% hydrogen peroxide solution (1.5 ml) were added. After stirring the reaction solution at room temperature for another 15 minutes, the reaction mixture was poured into saturated aqueous ammonium chloride solution, and the resultant was extracted with ethyl acetate. The organic layer was washed with water and with saturated brine, and dried 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: cyclohexane/ethyl acetate=3/1-2/1) to obtain the desired compound (1.42 g, yield: 59%).

Provenance & Evidence