反应详情

1,1-Cyclopropanedicarboxylic acid (5.02 g) was dissolved in tetrahydrofuran (50 ml) under a nitrogen atmosphere, and triethylamine (5.38 ml) was added dropwise with stirring and cooling in an ice water bath. After stirring at the same temperature for 30 minutes, thionyl chloride (2.82 ml) was added dropwise with cooling in ice water bath. After stirring at the same temperature for 30 minutes, a solution of benzyl alcohol (4.39 ml) in tetrahydrofuran (25 ml) was added with cooling in an ice water bath, and the reaction mixture was gradually brought to room temperature and stirred overnight. A 2N aqueous solution of sodium hydroxide (100 ml) was added to the reaction mixture, and tetrahydrofuran was distilled off under reduced pressure. tert-Butyl methyl ether (25 ml) was added to the resultant aqueous solution, followed by stirring. The organic layer and the aqueous layer were separated. The aqueous layer was cooled in an ice water bath, and 2N hydrochloric acid (50 ml) was added to adjust pH 4. Ethyl acetate (150 ml) was added, and the reaction mixture was stirred for a while. The organic layer was separated, washed with brine, and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent was dried under reduced pressure to give the title compound (6.29 g, 74%) as a pale yellow oil.

1. temperaturecooling in an ice water bath
2. stirringAfter stirring at the same temperature for 30 minutes
3. stirringAfter stirring at the same temperature for 30 minutes
4. temperaturewith cooling in an ice water bath
5. customwas gradually brought to room temperature
6. stirringstirred overnight
7. distillationwas distilled off under reduced pressure
8. additiontert-Butyl methyl ether (25 ml) was added to the resultant aqueous solution
9. stirringby stirring
10. customThe organic layer and the aqueous layer were separated
11. temperatureThe aqueous layer was cooled in an ice water bath
12. addition2N hydrochloric acid (50 ml) was added
13. additionEthyl acetate (150 ml) was added
14. stirringthe reaction mixture was stirred for a while
15. customThe organic layer was separated
16. washwashed with brine
17. dry with materialdried over anhydrous sodium sulfate
18. customThe residue obtained
19. distillationby distilling off the solvent
20. customwas dried under reduced pressure