toluene-4-sulfonic acid in benzene 5 h; Heating;

toluene-4-sulfonic acid in N,N-dimethyl-formamide; benzene 30 h; Heating;

Amberlite.(R). resin IR 120 (H) in N,N-dimethyl-formamide; benzene 5 h; Reflux;

1: NaBH4 / ethanol / 12 h 2: 82 percent / sodium periodate / ethanol; H2O / 0.25 h 3: 90 percent / pyridine / 1.) cooling with CCl4-solid CO2, 25 min, 2.) room temperature, overnight 4: 26 percent / p-TsOH / benzene / 10 h / Heating View Scheme

1: 96 percent / methanol / 1 h / 0 °C 2: 1) oxalyl chloride, DMSO, 2) triethylamine / 1) CH2Cl2, 40 min, -60 deg C, 2) 10 min, -60 deg C 3: POCl3, pyridine / Ambient temperature 4: 82 percent / NaBH4 / methanol / 1.5 h / 0 °C 5: 82 percent / OsO4, trimethylamine-N-oxide, pyridine, water / 2-methyl-propan-2-ol / 12 h / Heating 6: 100 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature 7: 86 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 1) -78 deg C, 1 h, 2) to 0 deg C, 12 h 8: 71 percent / triethylamine, 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / CH2Cl2 / 6 h / 0 °C 9: 75 percent / diisobutylaluminium hydride (DIBAL-H) / tetrahydrofuran / 1 h / 0 °C 10: 95 percent / pyridine, N,N-dimethylaminopyridine (DMAP) / CH2Cl2 / 12 h / Ambient temperature 11: 80 percent / pyridinium chlorochromate, 3 Angstroem molecular sieves / CH2Cl2 / 12 h / Ambient temperature 12: 100 percent / 50percent aq. CF3COOH / 4 h / Ambient temperature View Scheme