potassium hydroxide in tetrahydrofuran; methanol T=20°C; 1 h;

1.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C 1.2: 72 percent / I2 / tetrahydrofuran; pentane / 0.5 h / 20 °C 2.1: 64 percent / CuI; iPr2NH / Cl2Pd(PPh3)2 / toluene / 20 h / 65 °C 3.1: 98 percent / KOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1: 64 percent / CuI; iPr2NH / Cl2Pd(PPh3)2 / toluene / 20 h / 65 °C 2: 98 percent / KOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1.1: 84 percent / 15-crown-5; NaH / tetrahydrofuran / 20 h / Heating 2.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C 2.2: 72 percent / I2 / tetrahydrofuran; pentane / 0.5 h / 20 °C 3.1: 64 percent / CuI; iPr2NH / Cl2Pd(PPh3)2 / toluene / 20 h / 65 °C 4.1: 98 percent / KOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme

1.1: 84 percent / 15-crown-5; NaH / tetrahydrofuran / 20 h / Heating 2.1: t-BuLi / tetrahydrofuran; pentane / 1 h / -78 °C 2.2: 72 percent / I2 / tetrahydrofuran; pentane / 0.5 h / 20 °C 3.1: 64 percent / CuI; iPr2NH / Cl2Pd(PPh3)2 / toluene / 20 h / 65 °C 4.1: 98 percent / KOH / tetrahydrofuran; methanol / 1 h / 20 °C View Scheme