反应详情

温度

95 °C

To a solution of 7-bromo-1,2,3,4-tetrahydro-naphthalen-1-ol (0.708 g, 3.11 mmol), which can be prepared as described in Example 5, in DMF (6.5 mL) is added zinc cyanide (0.274 g, 2.33 mmol). Four evacuation-nitrogen fill cycles are performed and tetrakis(triphenylphosphine) palladium (0.072 g, 0.062 mmol) is added. The mixture is heated to 95° C. until the reaction is complete, whereupon water and diethyl ether are added. The mixture is filtered through Celite® and the organic phase is washed with water, dried with MgSO4, filtered and concentrated to give 7-cyano-1,2,3,4-tetrahydro-naphthalen-1-ol; 1H NMR (400 MHz, CDCl3) δ ppm 1.76-1.92 (m, 2 H), 1.95-2.13 (m, 2 H), 2.73-2.94 (m, 2 H), 4.77-4.80 (m, 1 H), 7.20 (d, J=8.0 Hz, 1 H), 7.46 (dd, J=8.0, 1.6 Hz, 1 H), 7.79 (br. s, 1 H).

1. additionare added
2. filtrationThe mixture is filtered through Celite®
3. washthe organic phase is washed with water
4. dry with materialdried with MgSO4
5. filtrationfiltered
6. concentrationconcentrated