反应详情

To a solution of 1,2,3,4-tetrahydroisoquinolinecarboxylic acid benzyl ester p-toluenesulfonate (2.1 g, 4.9 mmol) in acetonitrile (15 mL) were added 5-chloromethylfuran-2-carboxylic acid ethyl ester (0.50 mL, 3.3 mmol) and N,N-diisopropylethylamine (1.4 mL, 8.1 mmol), and the mixture was stirred at room temperature for 20 hours. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in ethyl acetate, and washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine. The organic layer was dried over anhydrous sodium sulfate, and concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=92/8) to give the title compound (1.1 g, 2.6 mmol, 81%).

1. concentrationThe reaction mixture was concentrated under reduced pressure
2. dissolutionthe obtained residue was dissolved in ethyl acetate
3. washwashed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
4. dry with materialThe organic layer was dried over anhydrous sodium sulfate
5. concentrationconcentrated under reduced pressure
6. customthe obtained residue was purified by silica gel column chromatography (hexane/ethyl acetate=92/8)