hydrogenchloride in 1,4-dioxane T=20°C; Inert atmosphere;

1.1: N,N,N',N'-tetraethyl ethylenediamine; n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 - -10 °C / Inert atmosphere 1.2: 1 h / -78 - 20 °C 1.3: -10 °C / pH 2 - 3 2.1: methanol / 20 °C / Inert atmosphere 3.1: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere View Scheme

1.1: sodium hexamethyldisilazane / tetrahydrofuran / 0.08 h / 0 °C / Inert atmosphere 1.2: 1 h / 0 - 20 °C 2.1: N,N,N',N'-tetraethyl ethylenediamine; n-butyllithium / hexane; tetrahydrofuran / 2 h / -78 - -10 °C / Inert atmosphere 2.2: 1 h / -78 - 20 °C 2.3: -10 °C / pH 2 - 3 3.1: methanol / 20 °C / Inert atmosphere 4.1: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere View Scheme

1: methanol / 20 °C / Inert atmosphere 2: hydrogenchloride / 1,4-dioxane / 20 °C / Inert atmosphere View Scheme