Sodium Methoxide → HCID 24988170, compound

Participants

Reaction Steps

To a liquid prepared by dissolving with stirring 6.7 g (0.045 mol, 0.95 eq.) of 2-mercaptobenzimidazole and 52.5 g (0.273 mol, 5.8 eq.) of a 28% sodium methoxide solution in 350 mL of methanol, a liquid prepared by dissolving the whole amount of 4-octyloxy-2-chloromethyl-3-methylpyridine in 180 mL of methanol was added at 27° C. Subsequently, the mixture was heated to reflux for one hour and cooled, and then methanol was solid dried under reduced pressure. A brown oily residue resulting therefrom was dissolved in 250 mL of ethyl acetate, and then the organic layer was washed with 100 mL of water. The organic layer was dried over anhydrous magnesium sulfate, and then concentrated to dryness. The resulting residue was purified by silica gel column chromatography, and then was concentrated to dryness, to obtain 14.9 g of an orange-colored oily matter. The orange-colored oily matter was recrystallized from ethyl acetate (5 vol.), to obtain 5.8 g of colorless crystals (HPLC: 98.8 Area %, yield 32.2%).

Provenance & Evidence