tetrabutyl ammonium fluoride in tetrahydrofuran T=45°C; 3 h;

1.1: 86 percent / imidazole / dimethylformamide / 24 h / 20 °C 2.1: n-BuLi / tetrahydrofuran / 0.33 h / -80 °C 2.2: 68 percent / HMPA / tetrahydrofuran / 0 °C 3.1: 99 percent / nBu4NF / tetrahydrofuran / 3 h / 45 °C View Scheme

1.1: n-BuLi / tetrahydrofuran / 0.33 h / -80 °C 1.2: 68 percent / HMPA / tetrahydrofuran / 0 °C 2.1: 99 percent / nBu4NF / tetrahydrofuran / 3 h / 45 °C View Scheme

1.1: 78 percent / KOH / dimethylsulfoxide / 16 h / 80 °C 2.1: Mg; mercury(II) chloride / diethyl ether / 0.5 h / Heating 2.2: 78 percent / diethyl ether / 0.33 h / -80 °C 3.1: 86 percent / imidazole / dimethylformamide / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran / 0.33 h / -80 °C 4.2: 68 percent / HMPA / tetrahydrofuran / 0 °C 5.1: 99 percent / nBu4NF / tetrahydrofuran / 3 h / 45 °C View Scheme

1.1: 78 percent / KOH / dimethylsulfoxide / 16 h / 80 °C 2.1: Mg; mercury(II) chloride / diethyl ether / 0.5 h / Heating 2.2: 78 percent / diethyl ether / 0.33 h / -80 °C 3.1: 86 percent / imidazole / dimethylformamide / 24 h / 20 °C 4.1: n-BuLi / tetrahydrofuran / 0.33 h / -80 °C 4.2: 68 percent / HMPA / tetrahydrofuran / 0 °C 5.1: 99 percent / nBu4NF / tetrahydrofuran / 3 h / 45 °C View Scheme

1.1: Mg; mercury(II) chloride / diethyl ether / 0.5 h / Heating 1.2: 78 percent / diethyl ether / 0.33 h / -80 °C 2.1: 86 percent / imidazole / dimethylformamide / 24 h / 20 °C 3.1: n-BuLi / tetrahydrofuran / 0.33 h / -80 °C 3.2: 68 percent / HMPA / tetrahydrofuran / 0 °C 4.1: 99 percent / nBu4NF / tetrahydrofuran / 3 h / 45 °C View Scheme