Grubb's 2nd generation catalyst in toluene T=80°C; 3 h;

nickel in ethanol 1 h;

1: 100 percent / toluene / 12 h / 20 °C 2: 100 percent / NaBH4 / methanol / 0.5 h / 20 °C 3: 94 percent / TFA / CHCl3 / 0.5 h / 20 °C 4: 100 percent / H2 / Pd/C / 10 h / 20 °C / 3102.89 Torr 5: 70 percent / K2CO3 / CH2Cl2 / 24 h / 20 °C 6: DIBAL-H / CH2Cl2 / 2 h / -79 °C 7: tetrahydrofuran / 12 h / 20 °C 8: 90 percent / Grubbs' 2nd. generation catalyst / toluene / 3 h / 80 °C View Scheme

1: 94 percent / TFA / CHCl3 / 0.5 h / 20 °C 2: 100 percent / H2 / Pd/C / 10 h / 20 °C / 3102.89 Torr 3: 70 percent / K2CO3 / CH2Cl2 / 24 h / 20 °C 4: DIBAL-H / CH2Cl2 / 2 h / -79 °C 5: tetrahydrofuran / 12 h / 20 °C 6: 90 percent / Grubbs' 2nd. generation catalyst / toluene / 3 h / 80 °C View Scheme

1: 100 percent / NaBH4 / methanol / 0.5 h / 20 °C 2: 94 percent / TFA / CHCl3 / 0.5 h / 20 °C 3: 100 percent / H2 / Pd/C / 10 h / 20 °C / 3102.89 Torr 4: 70 percent / K2CO3 / CH2Cl2 / 24 h / 20 °C 5: DIBAL-H / CH2Cl2 / 2 h / -79 °C 6: tetrahydrofuran / 12 h / 20 °C 7: 90 percent / Grubbs' 2nd. generation catalyst / toluene / 3 h / 80 °C View Scheme

1: 90 percent / 1.) HCl; 2.) NaBH4 / H2O; methanol / 3.5 h / Ambient temperature 2: 45 percent / 50percent AcOH / 72 h / Ambient temperature View Scheme

phosphorus pentoxide in toluene 4 h; Heating;

1: 80 percent 2: 52 percent / m-chloroperbenzoic acid 3: 1.) (CF3CO)2O; 2.) aq HCl / 2.) MeOH, 6 h, RT 4: 54 percent / NaBH4 / methanol View Scheme

1: 98 percent / methanol / 2.17 h / 28 °C 2: 94 percent / p-TsOH*H2O / benzene / 3 h / Heating 3: 69 percent / NaBH3CN, glacial AcOH / 0.5 h / 28 °C 4: 92 percent / POCl3, pyridine / 0.5 h / 80 - 90 °C 5: 74 percent / Raney Ni / ethanol / 1 h View Scheme

1: 98 percent / methanol / 2.17 h / 28 °C 2: 94 percent / p-TsOH*H2O / benzene / 3 h / Heating 3: 69 percent / NaBH3CN, glacial AcOH / 0.5 h / 28 °C 4: 92 percent / POCl3, pyridine / 0.5 h / 80 - 90 °C 5: 74 percent / Raney Ni / ethanol / 1 h View Scheme