反应详情

温度

-40 °C

To a solution of 4-(8-hydroxy-1,4-dioxaspiro[4.5]dec-8-yl)benzonitrile (7.8 g) in methylene chloride (100 mL) was added triethylamine (21 mL) at room temperature. The solution was cooled down to −40° C. and then mesyl chloride (4.7 mL) was added dropwise. The reaction mixture was stirred at −40° C. for 30 min, then warmed up to room temperature gradually and continuously stirred overnight. The reaction was quenched with sat. aqueous NaHCO3 solution. The aqueous layer was extracted with methylene chloride. The combined organic extracts were washed with brine, dried with Na2SO4, then evaporated. The residue was purified by column (Hex/EtOAc=5/1) to give the product 5.2 g as a white solid (yield: 71%): 1H NMR (CDCl3) δ 7.62-7.55 (2H, m), 7.50-7.45 (2H, m), 6.17-6.13 (1H, m), 4.02 (4H, s), 2.68-2.62 (2H, m), 2.53-2.47 (2H, m), 1.96-1.92 (2H, m); MS: 242 (M+1)+.

1. temperaturewarmed up to room temperature gradually
2. customcontinuously stirred overnight
3. customThe reaction was quenched with sat. aqueous NaHCO3 solution
4. extractionThe aqueous layer was extracted with methylene chloride
5. washThe combined organic extracts were washed with brine
6. dry with materialdried with Na2SO4
7. customevaporated
8. customThe residue was purified by column (Hex/EtOAc=5/1)