copper(ll) bromide in acetonitrile T=20°C; 2 h;

in chloroform

acetic acid in tetrahydrofuran T=26°C; 1.75 h;

hydrogen in water; decalin T=100°C; P=10351 Torr; 3 h;

tetrahydrofuran

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 6: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 8: 50 percent / mercuric acetate / 16 h / Heating 9: 80 percent / 0.58 h / 180 °C / sealed tube 10: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 11: Et3N / CH2Cl2 / 0 °C 12: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C 13: 80 percent / PTS / methanol / 4 h View Scheme

pyridinium chlorochromate absorbed on neutral alumina in dichloromethane 2 h; Ambient temperature;

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: 72 percent / PCC 2: 2.) H2SO4 / 1.) r.t.; 3 d; 2.) r.t., 8 h 3: 1.) p-TsOH; 2.) TsCl, NaI; 3.) AgNO2 View Scheme

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 6: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature 7: 70 percent / Mg / tetrahydrofuran / a. ice-cooled solution, 10 min b. overnight room temperature c. 3h reflux 8: 50 percent / mercuric acetate / 16 h / Heating 9: 80 percent / 0.58 h / 180 °C / sealed tube 10: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. 1h reflux 11: Et3N / CH2Cl2 / 0 °C 12: 1.) cuprous iodide / 1.) Et2O, -10 deg C, 1o min 2. 4h, 0 deg C View Scheme