反应详情

Commercially available 1-bromo-3-methoxypropane (24.0 g, 157 mmol) was added to a solution of commercially available 3,4-dihydroxybenzaldehyde (21.7 g, 157 mmol) and sodium carbonate (25.0 g, 236 mmol) in N,N-dimethylformamide (50 mL) under nitrogen atmosphere at room temperature. The reaction liquid was stirred at room temperature for 3 days and 4 hours. 2 M hydrochloric acid, ethyl acetate, and water were added to the reaction liquid at 0° C. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed serially with water and a saturated saline solution and then dried over anhydrous sodium sulfate. The drying agent was separated by filtration and the filtrate was concentrated under vacuum. The insoluble matters were separated by filtration with dichloromethane and the filtrate was concentrated under vacuum. The residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1) to obtain the title compound (17.2 g, 52%).

1. customThe reaction liquid
2. extractionThe aqueous layer was extracted with ethyl acetate
3. washThe combined organic layer was washed serially with water
4. dry with materiala saturated saline solution and then dried over anhydrous sodium sulfate
5. customThe drying agent was separated by filtration
6. concentrationthe filtrate was concentrated under vacuum
7. customThe insoluble matters were separated by filtration with dichloromethane
8. concentrationthe filtrate was concentrated under vacuum
9. customThe residue was purified with silica gel column chromatography (n-heptane:ethyl acetate=17:3-1:1)