diisobutylaluminium hydride in diethyl ether; benzene

oxalyl dichloride; dimethyl sulfoxide in dichloromethane T=-60 - -50°C; 0.5 h;

1: TsOH / tetrahydrofuran 2: (COCl)2; DMSO; Et3N View Scheme

[Rh(acac)2(CO)2]; polyoxyethanyl α-tocopheryl sebacate; hydrogen; 6-DPPon in water T=20°C; P=760.051 Torr; 24 h; Schlenk technique; regioselective reaction;

1: TsOH / tetrahydrofuran 2: (COCl)2; DMSO; Et3N View Scheme

potassium hydroxide; potassium permanganate in methanol T=0°C; 0.5 h;

pyridinium p-toluenesulfonate in dichloromethane

1: 91 percent / Amberlyst 15 / CH2Cl2 / 2 h / Ambient temperature 2: 83 percent / 1.) KOH, 2.) KMnO4 / methanol / 0.5 h / 0 °C View Scheme

1: 94 percent / Et3N / CH2Cl2 / 0.5 h / 0 °C 2: 2. H2O / 1. benzene, DMF, 16h reflux 3: 60 percent / NaOH / methanol / a) 24h b) H2O, 0 deg C, HCl 4: 90 percent / hexamethylphosphoric acid triamide / 3 h / 180 °C 5: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h 6: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature View Scheme

1: 90 percent / LiAlH4 / diethyl ether / a. reflux while adding reagent b. overnight room temperature c. reflux, 3h 2: 70 percent / pyridinium chlorochromate, NaOAc / CH2Cl2 / 3 h / Ambient temperature View Scheme