lithium aluminium tetrahydride in tetrahydrofuran T=20°C; 1 h;

1: 10 percent / LDA; ZnBr2 / tetrahydrofuran / -78 - 20 °C 2: aq. NaOH / dioxane / 1.5 h / 20 °C View Scheme

multistep reaction, various reaction conditions; Product distribution;

1.1: KHMDS / toluene / 0.25 h / 0 °C 1.2: 71 percent / toluene / 20 h / 20 °C 2.1: 85 percent / H2 / Pd/C / methanol / 20 °C 3.1: 62 percent / aq. NaIO4; RuCl3*3H2O / CCl4; acetonitrile / 24 h / 20 °C View Scheme

1: 1.) n-butyllithium / 11.) THF, hexane, -78 deg C, 1 h, 2.) THF, hexane, from -78 deg C to RT, 2 h 2: 1.) dicyclohexylborane, 2.) 30percent aq. H2O2, 10percent aq. NaOH / 1.) THF, from 0 deg C to RT, 1 h, 2.) THF, methanol, 0 deg C, 30 min. 3: 47 percent / HCl / dioxane / 1 h View Scheme