1: ethyl 2-benzenesulfonyldecanoate With sodium hexamethyldisilazane in tetrahydrofuran T=-78°C; 1 h; 2: methyl iodide in tetrahydrofuran T=-78 - -40°C;

1.1: NaH / dimethylformamide / 0.5 h / 0 °C 1.2: 85 percent / dimethylformamide / 0 - 20 °C 2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 96 percent / tetrahydrofuran / -78 - -40 °C View Scheme

1.1: NaH / dimethylformamide / 0.5 h / 0 °C 1.2: 85 percent / dimethylformamide / 0 - 20 °C 2.1: NaHMDS / tetrahydrofuran / 1 h / -78 °C 2.2: 96 percent / tetrahydrofuran / -78 - -40 °C View Scheme

diisobutylaluminium hydride in toluene T=-78°C; 0.333333 h;