1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 °C / |Inert atmosphere 1.2: 2 h / 0 - 20 °C / |Inert atmosphere 2.1: 1,10-phenanthroline; potassium tert-butylate / 1,3,5-trimethyl-benzene / 20 h / 110 °C / |Inert atmosphere; |Schlenk technique; |Sealed tube View Scheme

1.1: sodium hydride / N,N-dimethyl-formamide; mineral oil / 0.08 h / 0 °C / |Inert atmosphere 1.2: 2 h / 0 - 20 °C / |Inert atmosphere 2.1: 1,10-phenanthroline; potassium tert-butylate / 1,3,5-trimethyl-benzene / 20 h / 110 °C / |Inert atmosphere; |Schlenk technique; |Sealed tube View Scheme

1: 98 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene 2: 1) t-BuLi / 1) THF, below -90 deg C, 30 min 3: 92 percent / MnO2 / CH2Cl2 / 24 h / Ambient temperature 4: 88 percent / NaIO4 / H2O; dioxane 5: 85 percent / acetic anhydride / 0.5 h / Heating 6: 82 percent / p-toluenesulfonic acid / CH2Cl2 / Heating 7: 100 percent / Raney nickel / tetrahydrofuran / Heating 8: 100 percent / KOSi(CH3)3 / tetrahydrofuran / 0.25 h / Ambient temperature 9: 51 percent / NaH, LiBH4 / tetrahydrofuran / 2 h / Heating View Scheme

lithium aluminium tetrahydride; bromine in tetrahydrofuran; methanol; chloroform; ethyl acetate

1.1: dimethyl sulfoxide / 0.33 h / 50 - 90 °C 2.1: water; sodium hydroxide / ethanol / 18 h / Reflux 2.2: pH 2 View Scheme

acetic acid

18-crown-6 ether; potassium iodide in water; acetonitrile 10 h;

in dimethyl sulfoxide T=50 - 90°C; 0.333333 h;

in N,N-dimethyl-formamide T=20°C; Inert atmosphere;

1: 91 percent / Et4NI; iPr2NEt / acetonitrile / 0.5 h / 70 °C 2: 45 percent / P(o-tol)3; K2CO3; air / Pd(OAc)2 / dimethylformamide / 3 h / 125 °C View Scheme