Water → 1-Cyano-5,6-dimethoxy-3-phenyl-3,4-dihydronaphthalene

Participants

Reaction Steps

TMSCN (1.20 mL, 9.22 mmol) was added to a solution of phenyl tetralone 830 (2.00 g, 7.09 mmol) in dry toluene (100 mL). BF3.OEt2 (1.34 mL, 10.6 mmol) was then added slowly through a syringe and the reaction was stirred at ambient temperature overnight. The mixture was poured into cold H2O (100 mL) and extracted with EtOAc (3×50 mL). Column chromatography (2:1 EtOAc:hexanes) was used to purify the product and recover 0.674 g (2.39 mmol) of unreacted starting tetralone. The unsaturated nitrile (1.31 g, 4.50 mmol, 63.6%, 95.6% BRSM) was obtained as a white powder; mp 106-107° C. 1H NMR: (300 MHz, CDCl3): δ 7.36-7.21 (m, 6H, PhH, ArH); 6.84 (d, 1H, J=8.7 Hz, ArH); 6.78 (d, 1H, J=3.9 Hz, C═CH); 3.90 (s, 3H, ArOCH3); 3.81 (ddd, 1H, J=3.9, 7.2, 11.4 Hz, ArCH2CH); 3.71 (s, 3H, ArOCH3); 3.35 (dd, 1H, J=7.2, 16.5 Hz, ArCH2); 2.92 (dd, 1H, J=11.4, 16.5 Hz, ArCH2). EIMS: (M+)=291.

Provenance & Evidence