n-butyllithium in tetrahydrofuran; hexane T=-78 - 25°C; Substitution; Heating;

1: Trimethylene glycol With sodium hydride in tetrahydrofuran T=0°C; 0.5 h; 2: tert-butylchlorodiphenylsilane in tetrahydrofuran T=23°C; 16 h;

n-butyllithium in tetrahydrofuran; hexane T=-78 - 60°C; 35.25 h;

oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane T=-78 - 20°C; Swern oxidation; 1.75 h;

1.1: 1-hydroxy-3H-benz[d][1,2]iodoxole-1,3-dione / ethyl acetate / 5 h / Reflux 2.1: diethylzinc / hexane; dichloromethane / 3 h / 0 °C / Inert atmosphere 3.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.58 h / 0 °C / Inert atmosphere 3.2: Inert atmosphere View Scheme

1.1: oxalyl dichloride; dimethyl sulfoxide / dichloromethane / 1.25 h / -78 °C 1.2: 1 h / 22 °C 2.1: magnesium / tetrahydrofuran / 1.5 h / 0 °C 2.2: 2.58 h / 22 °C View Scheme