pyridine T=20°C; 0.5 h;

1.1: 3 h 2.1: n-butyllithium / tetrahydrofuran 2.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 3.1: lithium; ethylamine / 1 h / -5 °C 4.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 5.1: iodine; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 1 h / 0 °C 6.1: n-butyllithium / tetrahydrofuran 6.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 7.1: lithium; ethylamine / 1 h / -5 °C 8.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 9.1: 93 percent / pyridine / 0.5 h / 20 °C View Scheme

1: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h 2: pyridine; DMAP View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 1.2: tetrahydrofuran; hexane / 1 h / 0 °C 1.3: 58 percent / tetrahydrofuran; hexane / 1 h / 0 °C 2.1: 99 percent / PPTS / diethyl ether / 4 h / 60 °C 3.1: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h 4.1: pyridine; DMAP View Scheme

1: 99 percent / PPTS / diethyl ether / 4 h / 60 °C 2: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h 3: pyridine; DMAP View Scheme

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 1.2: tetrahydrofuran; hexane / 1 h / 0 °C 1.3: 58 percent / tetrahydrofuran; hexane / 1 h / 0 °C 2.1: 99 percent / PPTS / diethyl ether / 4 h / 60 °C 3.1: H2 / Pd/CaCO3 poisoned with Pb / hexane / 18 h 4.1: pyridine; DMAP View Scheme

1.1: n-butyllithium / tetrahydrofuran 1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 2.1: lithium; ethylamine / 1 h / -5 °C 3.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 4.1: 93 percent / pyridine / 0.5 h / 20 °C View Scheme

1.1: n-butyllithium / tetrahydrofuran 1.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 2.1: lithium; ethylamine / 1 h / -5 °C 3.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 4.1: iodine; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 1 h / 0 °C 5.1: n-butyllithium / tetrahydrofuran 5.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 6.1: lithium; ethylamine / 1 h / -5 °C 7.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 8.1: 93 percent / pyridine / 0.5 h / 20 °C View Scheme

1.1: HBr / toluene / 18 h / Heating 2.1: 3 h 3.1: n-butyllithium / tetrahydrofuran 3.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 4.1: lithium; ethylamine / 1 h / -5 °C 5.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 6.1: iodine; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 1 h / 0 °C 7.1: n-butyllithium / tetrahydrofuran 7.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 8.1: lithium; ethylamine / 1 h / -5 °C 9.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 10.1: 93 percent / pyridine / 0.5 h / 20 °C View Scheme

1.1: iodine; triphenylphosphine; imidazole / diethyl ether; acetonitrile / 1 h / 0 °C 2.1: n-butyllithium / tetrahydrofuran 2.2: tetrahydrofuran; hexamethylphosphoric acid triamide / 1 h / 20 °C 3.1: lithium; ethylamine / 1 h / -5 °C 4.1: p-toluenesulfonic acid / ethanol / 3 h / Heating 5.1: 93 percent / pyridine / 0.5 h / 20 °C View Scheme