lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 0.5 h;

1.1: 96 percent / imidazole / CH2Cl2 / 14 h / 20 °C 2.1: 99 percent / sodium hydroxide / ethanol; H2O / 6 h / 20 °C 3.1: 100 percent / oxalyl chloride / CH2Cl2 / 15 h / 20 °C 4.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 4.2: tetrahydrofuran; hexane / 1 h / -78 °C 5.1: 2.94 mg / NaBH4 / ethanol / -78 - 20 °C 6.1: 93 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C View Scheme

1.1: diethylzinc / hexane; dichloromethane / 3 h / 0 °C / Inert atmosphere 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 0.58 h / 0 °C / Inert atmosphere 2.2: Inert atmosphere View Scheme

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: 100 percent / oxalyl chloride / CH2Cl2 / 15 h / 20 °C 2.1: n-BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: tetrahydrofuran; hexane / 1 h / -78 °C 3.1: 2.94 mg / NaBH4 / ethanol / -78 - 20 °C 4.1: 93 percent / LiAlH4 / tetrahydrofuran / 0.5 h / 0 °C View Scheme