methanol; potassium hydroxide

lithium perchlorate in water; acetonitrile Oxidation; demethylation; Electrochemical reaction;

1: ammonium cerium (IV) nitrate / water; acetonitrile / 20 °C / Inert atmosphere 2: 4-(N,N-dimethlyamino)pyridine; triethylamine; zinc / 20 °C / Inert atmosphere 3: ammonium cerium (IV) nitrate / water; acetonitrile / 20 °C / Inert atmosphere View Scheme

bromine in chloroform 2 h; Ambient temperature;

ammonium cerium(IV) nitrate; water in acetonitrile

lead(IV) acetate in benzene T=60°C; 1 h;

in benzene T=60°C; 1 h;

1: 57 percent / n-BuLi / tetrahydrofuran / 0.05 h / 0 °C 2: 98 percent / Bu4NF / tetrahydrofuran / 1 h / Ambient temperature 3: 95 percent / DMSO, Et3N / CH2Cl2 / -60 deg C then warming up to 0 deg C 4: DIBAL / toluene / 0.33 h / -78 °C 5: 90 percent / (i-Pr)2NEt / tetrahydrofuran / 3 h / Heating 6: 94 percent / LiAlH4 / diethyl ether / 1 h / Heating 7: 72 percent / CAN / ethanol; H2O / -40 - 0 °C 8: Na2S2O4 / CHCl3; H2O / Ambient temperature 9: Me3SiBr / CH2Cl2 / 0.17 h / Heating 10: AcOK / ethanol / 0.33 h / Ambient temperature 12: 85 percent / tetrahydrofuran / 0.5 h / Ambient temperature 13: 85 percent / DDQ, CSA / benzene / 5 h / Heating 14: 87 percent / 1N HCl / 12 h / Heating View Scheme

1: 99 percent / POCl3 / CHCl3 / 6 h / Heating 2: 96 percent / tetrahydrofuran / 3 h / Ambient temperature 3: 1.) 60percent NaH, 2.) p-toluenesulfonic acid monohydrate / 1.) THF, r.t., overnight, 2.) acetone, 0-5 deg C, 3 h 4: 86 percent / diethyl ether; tetrahydrofuran / 3 h / Ambient temperature 5: 104 mg / SOCl2 / pyridine / 17 h / 0 - 5 °C 6: 5 percent / BBr3 / CH2Cl2 / 2 h / -70 °C View Scheme

trichlorophosphate in chloroform 10 h; Heating;