pyridine in hexane T=21 - 22°C; 16 - 18 h;

PTS monohydrate in acetic acid 1.) 30 min, 0 deg C 2.) 30 min, r.t.;

2,2'-azo-bisisobutyronitrile; tri-n-butyl-tin hydride in cyclohexane T=75°C; 1 h; Yield given;

1: 1) NaH / tetrahydrofuran / 1.) r. t., 6 h 3.) 50-55 deg C, 4 h 2: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 3: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 4: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 5: 70 percent / benzene / 10 h / Heating 6: 60 percent / KOH / methanol; H2O / 4 h / Heating 7: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h 8: 72 percent / 1) PTS monohydrate / acetic acid / 1.) 30 min, 0 deg C 2.) 30 min, r.t. View Scheme

1: 90 percent / H2 / Pt/C / ethanol / 3102.9 Torr / Ambient temperature 2: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 3: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 4: 70 percent / benzene / 10 h / Heating 5: 60 percent / KOH / methanol; H2O / 4 h / Heating 6: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h 7: 72 percent / 1) PTS monohydrate / acetic acid / 1.) 30 min, 0 deg C 2.) 30 min, r.t. View Scheme

pyridine in hexane T=21 - 23°C; 18 h; Title compound not separated from byproducts;

1: 63 percent / 1.8 N HCl in pentane / pentane / 0.08 h / -78 °C 2: azoisobutyronitrile, tributyltin hydride / cyclohexane / 1 h / 75 °C View Scheme

1: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 2: 70 percent / benzene / 10 h / Heating 3: 60 percent / KOH / methanol; H2O / 4 h / Heating 4: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h 5: 72 percent / 1) PTS monohydrate / acetic acid / 1.) 30 min, 0 deg C 2.) 30 min, r.t. View Scheme

1: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h 2: 72 percent / 1) PTS monohydrate / acetic acid / 1.) 30 min, 0 deg C 2.) 30 min, r.t. View Scheme

1: 65 percent / 1) LAH / diethyl ether / 1) kept overnight 2) 2 h reflux 2: 83 percent / triethylamine / CH2Cl2 / 0.5 h / -5 °C 3: 70 percent / benzene / 10 h / Heating 4: 60 percent / KOH / methanol; H2O / 4 h / Heating 5: 80 percent / tetrahydrofuran / 1.) r.t. 2.) reflux 2 h 6: 72 percent / 1) PTS monohydrate / acetic acid / 1.) 30 min, 0 deg C 2.) 30 min, r.t. View Scheme