1: K2CO3 / acetone / 16 h / Heating 2: LiAlH4 / tetrahydrofuran / 30 °C 3: PBr3; pyridine / CH2Cl2 4: K2CO3 / acetone / 16 h / Heating View Scheme

18-crown-6 ether; potassium carbonate in tetrahydrofuran 12 h; Heating;

1.1: 1-methyl-pyrrolidin-2-one / 18 h / 70 °C 2.1: K2CO3 / 1-methyl-pyrrolidin-2-one / 3 h / 140 °C 3.1: thionyl chloride / 1-methyl-pyrrolidin-2-one / 0.17 h / 0 °C 4.1: 1-methyl-pyrrolidin-2-one / 5 h / 120 °C 4.2: 80 percent / KOH / 1-methyl-pyrrolidin-2-one / 3 h / 120 °C View Scheme

sodium tetrahydroborate in tetrahydrofuran; methanol 17 h;

1: lithium bromide / tetrahydrofuran / Heating 2: 23 percent / K2CO3; 18-crown-6 / tetrahydrofuran / 12 h / Heating View Scheme

1: 96 percent / p-toluenesulfonic acid / 24 h / Heating 2: 80 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 12 h / Heating 3: 98 percent / LiAlH4 / tetrahydrofuran / 6.5 h / 0 - 20 °C 4: 88 percent / carbon tetrabromide; triphenylphosphine / tetrahydrofuran / 1 h / 20 °C 5: 85 percent / potassium iodide; potassium carbonate; [18]crown-6 / acetone / 10 h / Heating 6: 94 percent / LiAlH / tetrahydrofuran / 0 - 20 °C View Scheme

1.1: tetra-(n-butyl)ammonium iodide; potassium carbonate / 1,4-dioxane / 24 h / Reflux 2.1: lithium aluminium tetrahydride / tetrahydrofuran / 2 h / Inert atmosphere; Reflux 2.2: 20 °C View Scheme

carbon tetrabromide; triphenylphosphine