反应详情

Under nitrogen atmosphere, potassium t-butoxide (110 g, 0.78 mol) was added to a solution of di-t-butyl malonate (170 g, 0.78 mol) in t-butyl alcohol (1.5 L) in 3 portions at room temperature. After stirring at room temperature for 1 hour, the mixture was heated to 70° C. Then a solution of 2-chloromethyl-2-phenyloxirane (120 g) in tetrahydrofuran (500 mL) synthesized by the method described in J. Org. Chem. (1962, 27, 2241-2243) was added dropwise over 90 min. After stirring for 12 hours at 70° C., the mixture was cooled to room temperature and the solvent was evaporated. 10% Aqueous citric acid solution (500 mL) was added to the residue. The mixture was extracted with ethyl acetate (2.0 L), sequentially washed with water (500 mL) and saturated aqueous sodium chloride solution (200 mL), and dried over magnesium sulfate. After filtration and evaporation, the title compound (120 g, 3 step, yield 54%) was recrystallized from a mixed solution of hexane:diisopropyl ether=1:1 (600 mL) as a white solid.

1. temperaturethe mixture was heated to 70° C
2. addition(1962, 27, 2241-2243) was added dropwise over 90 min
3. stirringAfter stirring for 12 hours at 70° C.
4. temperaturethe mixture was cooled to room temperature
5. customthe solvent was evaporated
6. addition10% Aqueous citric acid solution (500 mL) was added to the residue
7. extractionThe mixture was extracted with ethyl acetate (2.0 L)
8. washsequentially washed with water (500 mL) and saturated aqueous sodium chloride solution (200 mL)
9. dry with materialdried over magnesium sulfate
10. filtrationAfter filtration and evaporation