1: 6-[(Tetrahydropyran-2-yl)oxy]-1bromohexane With magnesium in tetrahydrofuran T=20°C; 2: With dilithium tetrachlorocuprate in tetrahydrofuran T=-78°C; 3: 12-(p-iodophenyl)dodecyl tosylate in tetrahydrofuran T=-78 - 20°C; 15 h;

1.1: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 5 h / 20 °C 2.1: Mg / tetrahydrofuran / 20 °C 2.2: Li2CuCl4 / tetrahydrofuran / -78 °C 2.3: 64 percent / tetrahydrofuran / 15 h / -78 - 20 °C View Scheme

1.1: Mg / tetrahydrofuran / 20 °C 1.2: Li2CuCl4 / tetrahydrofuran / -78 °C 1.3: 55 percent / tetrahydrofuran / 17 h / -78 - 20 °C 2.1: 90 percent / pyridinium p-toluenesulfonate; ethanol / 3 h / 50 °C 3.1: 96 percent / N,N-(dimethylamino)pyridine / CH2Cl2 / 16 h 4.1: Mg / tetrahydrofuran / 20 °C 4.2: Li2CuCl4 / tetrahydrofuran / -78 °C 4.3: 64 percent / tetrahydrofuran / 15 h / -78 - 20 °C View Scheme

1.1: 92 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 5 h / 20 °C 2.1: Mg / tetrahydrofuran / 20 °C 2.2: Li2CuCl4 / tetrahydrofuran / -78 °C 2.3: 64 percent / tetrahydrofuran / 15 h / -78 - 20 °C View Scheme

1.1: 99 percent / pyridinium p-toluenesulfonate / CH2Cl2 / 5 h / 20 °C 2.1: Mg / tetrahydrofuran / 20 °C 2.2: Li2CuCl4 / tetrahydrofuran / -78 °C 2.3: 55 percent / tetrahydrofuran / 17 h / -78 - 20 °C 3.1: 90 percent / pyridinium p-toluenesulfonate; ethanol / 3 h / 50 °C 4.1: 96 percent / N,N-(dimethylamino)pyridine / CH2Cl2 / 16 h 5.1: Mg / tetrahydrofuran / 20 °C 5.2: Li2CuCl4 / tetrahydrofuran / -78 °C 5.3: 64 percent / tetrahydrofuran / 15 h / -78 - 20 °C View Scheme

1.1: 84 percent / bromotrimethylsilane / CH2Cl2 / 12 h / 20 °C 2.1: Mg / tetrahydrofuran / 20 °C 2.2: Li2CuCl4 / tetrahydrofuran / -78 °C 2.3: 55 percent / tetrahydrofuran / 17 h / -78 - 20 °C 3.1: 90 percent / pyridinium p-toluenesulfonate; ethanol / 3 h / 50 °C 4.1: 96 percent / N,N-(dimethylamino)pyridine / CH2Cl2 / 16 h 5.1: Mg / tetrahydrofuran / 20 °C 5.2: Li2CuCl4 / tetrahydrofuran / -78 °C 5.3: 64 percent / tetrahydrofuran / 15 h / -78 - 20 °C View Scheme

1.1: Mg / tetrahydrofuran / 20 °C 1.2: Li2CuCl4 / tetrahydrofuran / -78 °C 1.3: 55 percent / tetrahydrofuran / 17 h / -78 - 20 °C 2.1: 90 percent / pyridinium p-toluenesulfonate; ethanol / 3 h / 50 °C 3.1: 96 percent / N,N-(dimethylamino)pyridine / CH2Cl2 / 16 h 4.1: Mg / tetrahydrofuran / 20 °C 4.2: Li2CuCl4 / tetrahydrofuran / -78 °C 4.3: 64 percent / tetrahydrofuran / 15 h / -78 - 20 °C View Scheme