in N,N-dimethyl-formamide T=100°C; 1 h;

in acetonitrile T=22°C; Diels-Alder reaction; 0.25 h; regiospecific reaction;

in acetonitrile T=22°C; Diels-Alder reaction; 0.166667 h; regiospecific reaction;

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / Inert atmosphere 1.2: 0.5 h / 20 °C / Inert atmosphere 2.1: sodium periodate / dichloromethane / 2 h / 22 °C / Inert atmosphere 2.2: Inert atmosphere 3.1: acetonitrile / 0.17 h / 22 °C View Scheme

1.1: hydrogenchloride / methanol; dichloromethane; water / 3 h / 40 °C 2.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.75 h / 20 °C / Inert atmosphere 2.2: 0.5 h / 20 °C / Inert atmosphere 3.1: sodium periodate / dichloromethane / 2 h / 22 °C / Inert atmosphere 3.2: Inert atmosphere 4.1: acetonitrile / 0.17 h / 22 °C View Scheme