反应详情

温度

-78 °C

Under argon, a solution of diisopropylamine (3.36 ml, 24 mmol) in 20 ml of dry THF was cooled to 0° C. and admixed with butyllithium (9.6 ml, 24 mmol, 2.5 M in hexane). The solution was stirred with ice-cooling for 15 min, cooled to −78° C. and admixed with a solution of hexahydro-benzofuran-2-one (2.8 g, 20 mmol) in 10 ml of THF. This mixture was stirred at −78° C. for 1 h, and a solution of 2-bromomethylnaphthalene (5.31 g, 24 mmol) in 20 ml of THF was then added. The mixture was stirred at −78° C. for another 2 h and then at room temperature overnight. Water was then added, the organic solvent was removed under reduced pressure and the aqueous phase was extracted with MTBE. The combined ether phases were dried over magnesium sulphate, filtered and concentrated. Purification was carried out by column chromatography. Yield: 2.5 g (44.6%). Rf (cyclohexane/ethyl acetate 3:1)=0.69, Rf (cyclohexane/ethyl acetate 1:1)=0.83 MS (CI): m/e=281 [M+H+]

1. temperaturecooling for 15 min
2. stirringThis mixture was stirred at −78° C. for 1 h
3. stirringThe mixture was stirred at −78° C. for another 2 h
4. customat room temperature
5. customovernight
6. customthe organic solvent was removed under reduced pressure
7. extractionthe aqueous phase was extracted with MTBE
8. dry with materialThe combined ether phases were dried over magnesium sulphate
9. filtrationfiltered
10. concentrationconcentrated
11. customPurification