Water → HCID 67287853, compound

Participants

Reaction Conditions

Reaction Steps

Under an argon atmosphere, an n-butyllithium-hexane solution (1.60 mol/L, 11.16 mL) was added at −78° C. to a solution of (5R)-2-allyl-3,6-dimethoxy-5-isopropyl-2,5-dihydropyrazine (3.64 g) in tetrahydrofuran (60 mL) to form a reaction solution. This reaction solution was then stirred at −78° C. for 30 minutes. A solution of 4-bromo-2-chloro-1-(2-iodoethyl)benzene (6.73 g) in tetrahydrofuran (20 mL) was added to the reaction solution, and the reaction solution was stirred at −78° C. for 30 minutes and then at 0° C. for 1 hour. Water was added to the reaction solution, and the reaction solution was extracted with ethyl acetate. The extract was washed with water and saturated brine in that order, and then dried over anhydrous sodium sulfate. The anhydrous sodium sulfate was removed by filtration, and then the solvent was removed by distillation under reduced pressure. The resultant product was purified by silica gel column chromatography (hexane:ethyl acetate=70:1) to obtain the target product (6.04 g) as a colorless oil.

Provenance & Evidence