1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.5 h / Heating 1.2: tetrahydrofuran / 0.5 h / 0 °C 2.1: aq. H2O2; aq. NaHCO3 / methanol; tetrahydrofuran / 2.5 h / 70 °C 3.1: 1.14 g / H2 / 5 percent Pd/C / ethanol / 6.5 h / 50 °C 4.1: methanol / 2 h / 20 °C View Scheme

1: Li / tetrahydrofuran / -55 °C 2: 97 percent / H2 / Pd(OH)2/C / 760 Torr 3: Et3N 4: KOH / methanol View Scheme

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.5 h / Heating 1.2: tetrahydrofuran / 0.5 h / 0 °C 2.1: aq. H2O2; aq. NaHCO3 / methanol; tetrahydrofuran / 2.5 h / 70 °C 3.1: 1.14 g / H2 / 5 percent Pd/C / ethanol / 6.5 h / 50 °C 4.1: methanol / 2 h / 20 °C 5.1: TEMPO; NaClO2; NaClO / aq. phosphate buffer; acetonitrile / 35 °C / pH 6.7 View Scheme

1: Li / tetrahydrofuran / -55 °C 2: 97 percent / H2 / Pd(OH)2/C / 760 Torr 3: Et3N 4: KOH / methanol View Scheme

1: 1.) BuLi / 1.) THF, -78 deg C, 30 min, 2.) THF, a) -78 deg C, 20 min, b) RT, 20 min 2: 66 percent / LiAlH4 / tetrahydrofuran / 5 h / Heating 3: 63 percent / Et3N, 4-(N,N-dimethylamino)pyridine / CH2Cl2 / 72 h / Ambient temperature 4: 77 percent / (MeCN)2PdCl2 / tetrahydrofuran / 72 h / Ambient temperature 5: 44 percent / 1.) O3, HCl, 2.) NaBH4 / multistep reaction, other 2-substituted alcohols; var. reaction conditions View Scheme

1.1: Mg; 1,2-dibromoethane / tetrahydrofuran / 0.5 h / Heating 1.2: tetrahydrofuran / 0.5 h / 0 °C 2.1: aq. H2O2; aq. NaHCO3 / methanol; tetrahydrofuran / 2.5 h / 70 °C 3.1: 1.14 g / H2 / 5 percent Pd/C / ethanol / 6.5 h / 50 °C 4.1: methanol / 2 h / 20 °C 5.1: TEMPO; NaClO2; NaClO / aq. phosphate buffer; acetonitrile / 35 °C / pH 6.7 View Scheme

1: Li / tetrahydrofuran / -55 °C 2: 97 percent / H2 / Pd(OH)2/C / 760 Torr 3: Et3N View Scheme

1: toluene / 2 h / -78 °C 2: 80 percent / conc. HCl / dioxane / 12 h / Heating 3: 89 percent / hydrogen / 20 percent Pd(OH)2-C / methanol; H2O View Scheme

magnesium chloride 1.) CH2Cl2, rt, 30 min; 2.) rt, 48 h.; Yield given. Multistep reaction;

1: 66 percent / LDA / tetrahydrofuran / -78 °C 2: 89 percent / H2 / 20percent Pd(OH)2/C / ethyl acetate / 760 Torr / Ambient temperature 3: 64 percent / H2 / Raney nickel / tetrahydrofuran / 760 Torr / Ambient temperature View Scheme