[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH2:7][C:8]2=O.[Li][C:15]#[N:16].C(P(=O)(OCC)OCC)#N.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH2:5][CH2:6][CH:7]=[C:8]2[C:15]#[N:16]
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.
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