pyridine in dichloromethane T=0°C;

1: 18-crown-6 / acetonitrile / 16 h / Ambient temperature 2: 1) Zn, BrCH2CH2Br, 3) CuCN, LiCl / 1) THF, 5 deg C, 3 h, 2) THF, -75 to -20 deg C, 3) THF, -70 deg C to RT, 14 h 3: 96 percent / K2CO3, MeOH / 1 h / Ambient temperature 4: 80 percent / pyridine / CH2Cl2 / 3 h / 0 °C View Scheme

1: 1) Zn, BrCH2CH2Br, 3) CuCN, LiCl / 1) THF, 5 deg C, 3 h, 2) THF, -75 to -20 deg C, 3) THF, -70 deg C to RT, 14 h 2: 96 percent / K2CO3, MeOH / 1 h / Ambient temperature 3: 80 percent / pyridine / CH2Cl2 / 3 h / 0 °C View Scheme

1: 96 percent / K2CO3, MeOH / 1 h / Ambient temperature 2: 80 percent / pyridine / CH2Cl2 / 3 h / 0 °C View Scheme