diethylamine in ethanol 0.5 h; Heating;

potassium carbonate; potassium iodide in acetonitrile T=20°C;

1: tetrahydrofuran / 0 °C 2: 90 percent / (CH3)S*BH3 / tetrahydrofuran / 24 h / Ambient temperature; THF*BH3 View Scheme

1: 71 percent / NaH / benzene; dimethylformamide / 3 h / Ambient temperature 2: 74 percent / K2CO3 / H2O / 1.) room temperature, 1 h, 2.) reflux, 30 min 3: 76 percent / potassium tert-butoxide / dimethylformamide / 5 h / 100 °C 4: 73 percent / 48 percent HBr (aq.), acetic anhydride / 120 h / Heating 5: 92 percent / P2S5 / pyridine / 48 h / Heating 6: 70 percent / methanolic sodium methoxide / 24 h / 60 °C 7: 52 percent / 1M potassium tert-butoxide / dimethylformamide / 0.5 h / Ambient temperature View Scheme

sodium hydrosulfite in water Heating;

1: 72 percent / sodium thionite / H2O / Heating 2: 57 percent / 0.17 h / 135 °C View Scheme

in tetrahydrofuran T=0°C;

sodium carbonate in acetone T=60°C;