3-chloro-benzenecarboperoxoic acid in chloroform Ambient temperature;

1: 86.7 percent / piperidine, AcOH / benzene / Heating 2: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 3: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature View Scheme

1: 1.) HMPA, 2.) DDQ / 1.) 100 deg C, 22 h, 2.) benzene, 30 min 2: 95.7 percent / m-CPBA / CHCl3 / Ambient temperature View Scheme

1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h View Scheme

1: DIBAL-H / toluene / 1 h / -74 °C 2: 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme

diisobutylaluminium hydride in dichloromethane; toluene T=-78°C; 0.5 h;

1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 3: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 4: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 5: 71.3 percent / acetonitrile / 14 h / Heating 6: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature 7: 1.) Et2BOMe, 2.) NaBH4 / 1.) THF, MeOH, -78 deg C, 30 min, 2.) THF, MeOH, 3 h View Scheme

1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 3: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 4: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h 5: 71.3 percent / acetonitrile / 14 h / Heating 6: 13 g / HF / acetonitrile / 1.5 h / Ambient temperature View Scheme

1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 3: 277 mg / DIBAL-H / toluene / 1 h / -74 °C View Scheme

1: 46.9 g / ethanol / 1 h / Ambient temperature 2: 1.) NaH / 1.) DMF, 30 min, 2.) DMF, RT, 2 h 3: 277 mg / DIBAL-H / toluene / 1 h / -74 °C 4: 71.2 percent / 4-methylmorpholine-N-oxide, tetrapropyl-ammonium perruthenate, molecular sieves 4 Angstroem / CH2Cl2 / 2 h View Scheme