thionyl chloride T=5 - 20°C; 16 h; Inert atmosphere;

1.1: ethanol; calcium chloride; sodium tetrahydroborate / 16 h / 5 - 20 °C / Inert atmosphere 1.2: 1 h / 20 °C 1.3: Cooling with ice 2.1: thionyl chloride / 16 h / 5 - 20 °C / Inert atmosphere View Scheme

1: Na2S / ethanol; H2O 2: H2O, PhICl2 / acetonitrile 3: Al2O3 / (heating) View Scheme

sodium carbonate in dichloromethane; water pH=7.5 - 8;