1.1: 11.68 g / LiAlH4 / tetrahydrofuran / 2.5 h / 0 °C 2.1: 91 percent / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 3.1: 57 percent / Br2; AcOH; KOAc / diethyl ether / 14 h / 0 - 20 °C 4.1: 59 percent / K2CO3 / methanol; CH2Cl2; H2O / 5 h / 80 °C 5.1: 95 percent / PCC / CH2Cl2 / 3 h / 20 °C 6.1: LDA / tetrahydrofuran / 0.17 h / 0 °C 6.2: CDCl3 / 12 h / 20 °C View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=0°C; 2.5 h;

1.1: 11.68 g / LiAlH4 / tetrahydrofuran / 2.5 h / 0 °C 2.1: 91 percent / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 3.1: BH3 / tetrahydrofuran / 2 h / 20 °C 3.2: 62 percent / aq. NaOH; aq. H2O2 / tetrahydrofuran / 1.5 h / 0 - 20 °C 4.1: 97 percent / PCC / CH2Cl2 / 3 h / 20 °C 5.1: 99 percent / HC(OEt)3; p-TSA / CH2Cl2 / 3.5 h / 20 °C 6.1: 51 percent / NaHCO3 / methanol; H2O / 72 h / 67 °C 7.1: 96 percent / PCC / CH2Cl2 / 3 h / 20 °C 8.1: PhSeCl / ethyl acetate / 3 h / 20 °C 8.2: 70 percent / aq. H2O2 / ethyl acetate / 0.5 h 9.1: 195 mg / pyridine; DMAP / CH2Cl2 / 3 h / 20 °C 10.1: 64 percent / aq. HCl / acetone / 0.5 h / 20 °C 11.1: 72 percent / K-Selectride / tetrahydrofuran / 5.5 h / -78 °C 12.1: POCl3; pyridine / 1 h / 20 °C 13.1: 250 mg / K2CO3 / methanol; H2O / 1 h / Heating 14.1: 37 percent / MnO2 / acetone / 12 h / 20 °C View Scheme