N-ethyl-N,N-diisopropylamine in N,N-dimethyl-formamide 6 h; Ambient temperature;

in N,N-dimethyl-formamide T=0°C; 3 h;

1: 79 percent / chromium(II) chloride / acetone; H2O / 0.25 h / 0 °C 2: 61 percent / dimethylformamide / 3 h / 0 °C View Scheme

1: lead tetra-acetate 2: 79 percent / chromium(II) chloride / acetone; H2O / 0.25 h / 0 °C 3: 61 percent / dimethylformamide / 3 h / 0 °C View Scheme

manganese(IV) oxide; lithium aluminium tetrahydride Multistep reaction;

1: H2O2, NaOH 2: 1.) HCl; 2.) pyridine 3: 1.) NaBH4, CeCl3; 2.) 4-dimethylaminopyridine 4: 1.) LiAlH4; 2.) MnO2 View Scheme

1: 1.) NaBH4, CeCl3; 2.) 4-dimethylaminopyridine 2: 1.) LiAlH4; 2.) MnO2 View Scheme

1: 1.) HCl; 2.) pyridine 2: 1.) NaBH4, CeCl3; 2.) 4-dimethylaminopyridine 3: 1.) LiAlH4; 2.) MnO2 View Scheme

1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min 2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C 4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C 6: 89 percent / 1,5-diazabicyclo<5.4.0>undec-5-ene / benzene / 18 h / Ambient temperature 7: 99 percent / H2O, AcOH / tetrahydrofuran / 24 h / Ambient temperature View Scheme

1: 1.) Mg, 2.) cuprous iodide / 1.) tetrahydrofuran, reflux, 4.5 h, 2.) -10 deg C, 10 min 2: 87 percent / lithium tri-s-butylborohydride / tetrahydrofuran / 3 h / -78 °C 3: 79 percent / toluene-p-sulphonic acid / CH2Cl2 / 3 h / 0 °C 4: 97 percent / tetrabutylammonium fluoride / tetrahydrofuran / 2.5 h / 0 °C 5: 100 percent / Jones reagent / acetone / 3.5 h / -20 °C 6: diethyl ether / 1 h 7: 81 percent / H2O, AcOH / tetrahydrofuran / 24 h / Ambient temperature View Scheme