formic acid 24 h; Ambient temperature;

1: 1.) NaH, 2.) TBAI, 15-crown-5 / 1.) toluene, from 60 to 70 deg C, 2 h, 2.) toluene, 80 deg C, 24 h 2: 1.) Sn2Bu6, Pd(PPh3)4, 2.) NaI, chloramine-T, AcONa / 1.) dioxane, reflux, 1.5 h, 2.) MeOH, H2O, RT, 30 min 3: 100 percent / 90percent aq. HCOOH / 24 h / Ambient temperature View Scheme

1: 1.) NaH, 2.) 15-crown-5 / 2.) toluene, reflux, 24 h 2: 2N HCl / tetrahydrofuran / 2 h / 70 °C View Scheme

1: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 2: 1.) NaH, 2.) 15-crown-5 / 2.) toluene, reflux, 24 h 3: 2N HCl / tetrahydrofuran / 2 h / 70 °C View Scheme

1: 81 percent / Et3N / acetonitrile / 12 h / Ambient temperature 2: 86 percent / LiAlH4 / tetrahydrofuran; diethyl ether / 2 h / Heating 3: 1.) NaH, 2.) 15-crown-5 / 2.) toluene, reflux, 24 h 4: 2N HCl / tetrahydrofuran / 2 h / 70 °C View Scheme

1: 56 percent / BF3*Et2O / cyclohexane; CH2Cl2 / 18 h / 60 - 70 °C 2: 1.) Sn2Bu6, Pd(PPh3)4, 2.) NaI, chloramine-T, AcONa / 1.) dioxane, reflux, 1.5 h, 2.) MeOH, H2O, RT, 30 min 3: 100 percent / 90percent aq. HCOOH / 24 h / Ambient temperature View Scheme

1: 1.) NaH, 2.) TBAI, 15-crown-5 / 1.) toluene, from 60 to 70 deg C, 2 h, 2.) toluene, 80 deg C, 24 h 2: 1.) Sn2Bu6, Pd(PPh3)4, 2.) NaI, chloramine-T, AcONa / 1.) dioxane, reflux, 1.5 h, 2.) MeOH, H2O, RT, 30 min 3: 100 percent / 90percent aq. HCOOH / 24 h / Ambient temperature View Scheme

1: 1.) Sn2Bu6, Pd(PPh3)4, 2.) NaI, chloramine-T, AcONa / 1.) dioxane, reflux, 1.5 h, 2.) MeOH, H2O, RT, 30 min 2: 100 percent / 90percent aq. HCOOH / 24 h / Ambient temperature View Scheme