1: 94 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 2: 2. H2O / 1. benzene, DMF, 16h reflux 3: 60 percent / NaOH / methanol / a) 24h b) H2O, 0 deg C, HCl 4: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 5: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h View Scheme

1: 2. H2O / 1. benzene, DMF, 16h reflux 2: 60 percent / NaOH / methanol / a) 24h b) H2O, 0 deg C, HCl 3: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 4: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h View Scheme

1: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 2: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h View Scheme

1: 60 percent / NaOH / methanol / a) 24h b) H2O, 0 deg C, HCl 2: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 3: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h View Scheme

2: 1.) magnesium / 1.) THF, reflux, 1.5 h, 2.) reflux, 1 h. View Scheme

magnesium 1.) THF, reflux, 1.5 h, 2.) reflux, 1 h.; Yield given. Multistep reaction;

1: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 2: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 3: 50 percent / mercuric acetate / 16 h / Heating 4: 80 percent / 0.58 h / 180 °C / sealed tube 5: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 6: Et3N / CH2Cl2 / 0 °C 7: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C 8: 80 percent / PTS / methanol / 4 h View Scheme

2,3'-bipyridine; ammonium hydroxide; copper(l) iodide; 2,2,6,6-tetramethyl-1-piperidinyloxy, free radical; oxygen in acetonitrile T=50°C; 24 h;

1: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 2: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 3: 50 percent / mercuric acetate / 16 h / Heating 4: 80 percent / 0.58 h / 180 °C / sealed tube 5: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 6: Et3N / CH2Cl2 / 0 °C 7: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C View Scheme