1: 74 percent / H2 / PtO2 / acetic acid / Ambient temperature 2: 2 h / 180 °C 3: 1.) POCl3, 2.) NaBH4 / 1.) toluene, reflux, 1 h; 2.) MeOH, room temp. View Scheme

1: 1.) C2H5MgBr / 1.) Et2O, 30 min, 2.) Et2O, 0 deg C, 1 h, room temp., 2 h 2: 74 percent / H2 / PtO2 / acetic acid / Ambient temperature 3: 2 h / 180 °C 4: 1.) POCl3, 2.) NaBH4 / 1.) toluene, reflux, 1 h; 2.) MeOH, room temp. View Scheme

1: 40 percent / LiAlH4 / diethyl ether / 3 h / Heating 2: 2 h / 180 °C 3: 1.) POCl3, 2.) NaBH4 / 1.) toluene, reflux, 1 h; 2.) MeOH, room temp. View Scheme

1: 18 percent / 7.5 N aq.HCl / ethanol / 0.17 h / Heating 2: 40 percent / LiAlH4 / diethyl ether / 3 h / Heating 3: 2 h / 180 °C 4: 1.) POCl3, 2.) NaBH4 / 1.) toluene, reflux, 1 h; 2.) MeOH, room temp. View Scheme

1: 50 percent / LiAlH4 / diethyl ether / Heating 2: 18 percent / 7.5 N aq.HCl / ethanol / 0.17 h / Heating 3: 40 percent / LiAlH4 / diethyl ether / 3 h / Heating 4: 2 h / 180 °C 5: 1.) POCl3, 2.) NaBH4 / 1.) toluene, reflux, 1 h; 2.) MeOH, room temp. View Scheme

sodium tetrahydroborate; trichlorophosphate 1.) toluene, reflux, 1 h; 2.) MeOH, room temp.; Yield given. Multistep reaction;

1: 2 h / 180 °C 2: 1.) POCl3, 2.) NaBH4 / 1.) toluene, reflux, 1 h; 2.) MeOH, room temp. View Scheme