hydrogenchloride 0.5 h; Ambient temperature;

1.1: 60.1 percent / POCl3 / 1 h / Heating 2.1: 61.74 percent / sodium / 3 h / Heating 3.1: lithium diisopropylamide / hexane; tetrahydrofuran / 0.5 h / -70 - -55 °C 3.2: tetrahydrofuran; hexane / 3 h / -55 - -10 °C 3.3: 67.92 percent / ammonium chloride (satd.) / tetrahydrofuran; hexane / -10 - 20 °C 4.1: 5.5 h / Heating 4.2: 23.3 percent / water / 20 °C View Scheme

1: 80 percent / HCl / H2O / 1 h / Heating 2: 57 percent / sodium hydride / dimethylformamide View Scheme

1.1: 80 percent / HCl / H2O / 1 h / Heating 2.1: 57 percent / sodium hydride / dimethylformamide 3.1: 59 percent / HBr; acetic acid / dioxane / 12 h / 20 °C 4.1: zinc; 1,2-dibromoethane; trimethylsilylchloride / tetrahydrofuran / 20 °C 4.2: 30 percent / (o-furyl)3P / bis(dibenzylideneacetone)palladium(0) / tetrahydrofuran / 12 h / 20 °C View Scheme

1: 63 percent / K2S2O8, AgNO3 / H2O / 1.) 90-100 deg C; 2.) room temp. 16 h 2: 40 percent / dimethylformamide / 96 h / Ambient temperature 3: 90 percent / NaOH / methanol; dioxane; H2O / 16 h / 40 °C 4: 1.) Triethylamine; 2.) Hydroxybenztriazole, DCC / DMF, room temp., 16 h 5: 63 percent / LiBH4 / 1,2-dimethoxy-ethane / 1.) -78 deg C; 2.) room temp., 2 h View Scheme