1: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h 2: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h 2: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 3: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 4: 50 percent / mercuric acetate / 16 h / Heating 5: 80 percent / 0.58 h / 180 °C / sealed tube 6: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 7: Et3N / CH2Cl2 / 0 °C 8: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C 9: 80 percent / PTS / methanol / 4 h View Scheme

lithium aluminium tetrahydride in diethyl ether a. reflux while adding reagent b. overnight room temperature c. reflux, 3h;

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