sodium hydride in N,N-dimethyl-formamide T=0 - 20°C; 12 h;

1.1: 85 percent / bromine / 2-methyl-propan-2-ol; H2O / 20 °C 2.1: 94 percent / zinc; acetic acid / 20 °C 3.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 3.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C 4.1: 54 percent / sodium hydride in oil / dimethylformamide / 12 h / 0 - 20 °C View Scheme

1.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 1.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C 2.1: 54 percent / sodium hydride in oil / dimethylformamide / 12 h / 0 - 20 °C View Scheme

1.1: 94 percent / zinc; acetic acid / 20 °C 2.1: borane*tetrahydrofurane / tetrahydrofuran / 0.58 h / 0 - 20 °C 2.2: 50 percent / manganese triacetate / acetic acid / 0.75 h / 75 °C 3.1: 54 percent / sodium hydride in oil / dimethylformamide / 12 h / 0 - 20 °C View Scheme