hydrogen; palladium on activated charcoal in methanol T=20°C; P=1034.3 - 2585.74 Torr;

1: chlorotrimethylsilane / 36 h / Heating 2: 93 percent / H2 / Pd/C / methanol / 760.05 Torr View Scheme

1: 74 percent / CSA / methanol 2: 97 percent / hydrogen / 10 percent Pd on carbon / 760 Torr View Scheme

1: O3 / methanol; CH2Cl2 / 2 h / -78 °C 2: 2.) camphorsulfonic acid / 1.) MeOH, CH2Cl2, room temp., 30 min; 2.) MeOH, CH2Cl2, room temp., 75 min 3: 97 percent / H2 / Pd/C / ethanol / Ambient temperature View Scheme

1: camphorsulfonic acid / 9 h / Heating 2: 97 percent / H2 / Pd/C / ethanol / Ambient temperature View Scheme

1: NaOAc, CuCl2 / H2O; acetone 2: O3 / methanol; CH2Cl2 / 2 h / -78 °C 3: 2.) camphorsulfonic acid / 1.) MeOH, CH2Cl2, room temp., 30 min; 2.) MeOH, CH2Cl2, room temp., 75 min 4: 97 percent / H2 / Pd/C / ethanol / Ambient temperature View Scheme

1: 84 percent / pyridine / 1 h / Ambient temperature 2: 82 percent / PPTS / benzene / 2 h / Heating View Scheme

1: 94 percent / Heating 2: 97 percent / POCl3; Et3N 3: 79 percent / diisopropylamine; butyllithium / bis-(2-methoxy-ethyl) ether / 1 h / -78 °C View Scheme

sodium tris(acetoxy)borohydride in acetic acid T=50°C; 18 h;

1.1: 83 percent / NaBH(OAc)3 / acetic acid / 19 h / 20 - 50 °C 2.1: 98 percent / H2 / Pd/C / methanol / 20 h / 2585.74 Torr 3.1: 97 percent / K2CO3 / dimethylformamide / 5 h / 20 - 50 °C 4.1: HCl gas / acetonitrile / 0.5 h / 0 - 20 °C 4.2: acetonitrile / 2 h / -10 - 0 °C 4.3: 86.5 percent / acetonitrile / 1 h / -10 - 0 °C 5.1: 75 percent / t-BuOK / tetrahydrofuran / -5 - 45 °C View Scheme