反应详情

温度

5 °C

5-Methoxy-1-tetralone (8.80 g) was dissolved in 50 ml of anhydrous THF and cooled to 5° C. under N2 atmosphere. LiCN (0.50 g.) was added to the stirred solution, followed by dropwise addition of diethyl cyanophosphonate (9.1 ml) over 10 min. After 45 min at 5° C., the reaction was poured into 200 ml H2O and extracted with EtOAc (3×100 ml) The combined organic extracts were washed with water (3×150 ml), saturated NaCl (150 ml), dried (MgSO4), and evaporated under reduced pressure. The resulting colorless oil was dissolved in benzene (100 ml) and p toluenesulfonic acid (0.50 g) was added. The reaction was stirred at reflux for 2 hr, cooled to room temperature, and poured into 5% NaHCO3 solution (150 ml). The reaction was extracted with Et2O (2×100 ml) and the combined organic extracts were washed with saturated NaCl solution (150 ml), dried (MgSO4), and evaporated under reduced pressure to yield 9.55 g of a white solid. The product was recrystallized from MeOH to yield 7.81 g of the product as white needles.

1. extractionextracted with EtOAc (3×100 ml) The combined organic extracts
2. washwere washed with water (3×150 ml), saturated NaCl (150 ml)
3. dry with materialdried (MgSO4)
4. customevaporated under reduced pressure
5. dissolutionThe resulting colorless oil was dissolved in benzene (100 ml)
6. additionp toluenesulfonic acid (0.50 g) was added
7. temperatureat reflux for 2 hr
8. temperaturecooled to room temperature
9. additionpoured into 5% NaHCO3 solution (150 ml)
10. extractionThe reaction was extracted with Et2O (2×100 ml)
11. washthe combined organic extracts were washed with saturated NaCl solution (150 ml)
12. dry with materialdried (MgSO4)
13. customevaporated under reduced pressure