pyridine; potassium permanganate 40 h; Heating;

pyridine; potassium permanganate in water

1.1: 98 percent / borane-THF complex / tetrahydrofuran / 10 - 20 °C 2.1: 75 percent / Pd(PPh3)4 / dimethylformamide / 18 h / 95 °C 3.1: 90 percent / Et3N; DMSO; pyridine*SO3 / CH2Cl2 / 2 h / 5 - 20 °C 4.1: EtMgBr / CH2Cl2 / 3 h / 20 °C 4.2: 98 percent / CH2Cl2 / 2 h / -78 - 20 °C 5.1: 100 percent / pyridine / dimethylformamide / 3 h 6.1: ethyl acetate / 60 °C 7.1: 0.838 g / MeOH / 1 h / Heating 8.1: 91 percent / aq. NaOH / tetrahydrofuran / 1 h / 20 °C View Scheme

1: 98 percent / borane-THF complex / tetrahydrofuran / 10 - 20 °C 2: 75 percent / Pd(PPh3)4 / dimethylformamide / 18 h / 95 °C 3: CBr4; PPh3 / CH2Cl2 / 3 h / 20 °C 4: 6.09 g / dimethylformamide / 20 °C View Scheme

thionyl chloride T=80°C; 5 h;

in methanol; hexanes; toluene T=0 - 20°C; 0.666667 h;

1: sodium tetrahydroborate; boron trifluoride diethyl etherate / tetrahydrofuran / 2 h / 20 °C 2: sodium acetate; pyridinium chlorochromate / dichloromethane / 2 h / 20 °C View Scheme

oxalyl dichloride in dichloromethane; N,N-dimethyl-formamide T=20°C;

sulfuric acid; potassium nitrate T=20°C;

1: 98 percent / borane-THF complex / tetrahydrofuran / 10 - 20 °C 2: 75 percent / Pd(PPh3)4 / dimethylformamide / 18 h / 95 °C 3: 90 percent / Et3N; DMSO; pyridine*SO3 / CH2Cl2 / 2 h / 5 - 20 °C View Scheme