反应详情

温度

45 °C

To a solution of (−)-nopol (Aldrich) (100 g, 0.60 mmol) in dimethoxy ethane (350 mL) was added NaH (60% oil dispersion, 31.1 g, 0.81 mmol). The mixture was refluxed for 2.5 hours, cooled to 45° C., and 2-chloroacetic acid (23.5 g 0.25 mmol) in dimethoxy ethane (180 mL) was added drop wise over a period of 1.5 hours. The reaction mixture was refluxed for 1 hour. After cooling at room temperature, water (75 mL) was added slowly, followed by 10% aqueous NaOH. The mixture was extracted with ether (1 L) (discarded), the aqueous phase was acidified and extracted with ether. The organic layer was dried over magnesium sulfate, filtered, and concentrated. The residue was distilled under reduced pressure to yield the title compound (29.5 g, 135-137° C. at 1.0 mm of Hg). n25D 1.4914, mp 78-80° C.

1. temperatureThe mixture was refluxed for 2.5 hours
2. temperatureThe reaction mixture was refluxed for 1 hour
3. temperatureAfter cooling at room temperature
4. extractionThe mixture was extracted with ether (1 L) (discarded)
5. extractionextracted with ether
6. dry with materialThe organic layer was dried over magnesium sulfate
7. filtrationfiltered
8. concentrationconcentrated
9. distillationThe residue was distilled under reduced pressure