Hydrogen Peroxide → HCID 23369640, compound

Participants

Reaction Steps

5-Methyl-2,3,6,7-tetrahydro-2-vinylfuro[2,3-f]quinoline-7-one (2.17 g) was suspended in tetrahydrofuran (40 ml). 9-Borabicyclo[3.3.1]nonan (0.5 mol, tetrahydrofuran solution, 80 ml) was added thereto while cooling on ice, and the mixture was stirred for 5.5 hours. Subsequently, aqueous 3N-NaOH solution (20 ml) and aqueous 35% hydrogen peroxide (20 ml) were added to the mixture in this order, and the temperature was raised to room temperature. After stirring for 30 minutes, extraction was performed with a solvent mixture of chloroform-methanol (4:1). The organic phase was dried and condensed under reduced pressure. The residue was recrystallized from a solvent mixture of chloroform-ethyl acetate-ether to obtain 1.7 g of 2-(2-hydroxyethyl)-5-methyl-2,3,6,7-tetrahydrofuro[2,3-f]quinoline-7-one as pale yellow powdery crystals (72.6%).

Provenance & Evidence