Water → 5-Methoxy-3,4-dihydronaphthalene-1-carbonitrile

Temperature

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 (MgSO 4), 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)
2. washThe combined organic extracts were 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 (MgSO 4)
13. customevaporated under reduced pressure

ORD record

ord-83fa0a10826349d794297a26e4164cce

Source dataset

uspto-grants-1992_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05140040