反应详情

To a solution of 1.208 g (7.735 mmol) of 2-[3-(2-hydroxyethyl)furan-2-yl]ethanol and 4.04 ml (23.2 mmol) of N,N-diisopropylethylamine in 50 ml of dichloromethane, 1.32 ml (17.0 mmol) of methanesulfonyl chloride was added dropwise under ice-cooling, followed by stirring at room temperature for 1 hour. The reaction mixture was poured into water and extracted with diethyl ether 3 times. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting residue was dissolved in 100 ml of ethanol; 0.83 g (7.7 mmol) of benzylamine and 2.37 ml (17.0 mmol) of triethylamine were added, followed by stirring at 80° C. for 3 days. After the solvent was distilled off from the reaction mixture under reduced pressure, aqueous sodium hydroxide was added, followed by 3 extractions with ethyl acetate. The combined organic layer was dried over anhydrous magnesium sulfate; the solvent was distilled off under reduced pressure. The resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1) to yield the desired product.

1. temperaturecooling
2. extractionextracted with diethyl ether 3 times
3. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
4. distillationthe solvent was distilled off under reduced pressure
5. dissolutionThe resulting residue was dissolved in 100 ml of ethanol
6. stirringby stirring at 80° C. for 3 days
7. distillationAfter the solvent was distilled off from the reaction mixture under reduced pressure, aqueous sodium hydroxide
8. additionwas added
9. extractionfollowed by 3 extractions with ethyl acetate
10. dry with materialThe combined organic layer was dried over anhydrous magnesium sulfate
11. distillationthe solvent was distilled off under reduced pressure
12. customThe resulting crude product was purified by silica gel column chromatography (hexane/ethyl acetate=9/1)