sodium hydride in N,N-dimethyl-formamide 21 h;

1.1: n-BuLi / tetrahydrofuran; hexane / 4 h / -78 - 20 °C 1.2: ZnCl2 / tetrahydrofuran; hexane / 1.25 h / -40 - 20 °C 1.3: tetrahydrofuran; hexane / 14 h / 0 - 20 °C 2.1: hydrazine monohydrate / methanol / 2 h 3.1: aqueous HCl / 14 h / pH 2 4.1: 31.9 g / thionyl chloride / 15 h 5.1: 63 percent / NaH / dimethylformamide; various solvent(s) / 21 h View Scheme

1: hydrazine monohydrate / methanol / 2 h 2: aqueous HCl / 14 h / pH 2 3: 31.9 g / thionyl chloride / 15 h 4: 63 percent / NaH / dimethylformamide; various solvent(s) / 21 h View Scheme

1: aqueous HCl / 14 h / pH 2 2: 31.9 g / thionyl chloride / 15 h 3: 63 percent / NaH / dimethylformamide; various solvent(s) / 21 h View Scheme