potassium tert-butylate in diethyl ether T=0°C; 0.5 h;

1: 97 percent / potassium t-butoxide / diethyl ether / 16 h / 1.) ether, 16 h 2: 87 percent / NaCl, water / dimethylsulfoxide / 10 h / 150 °C 3: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 66 percent / diethyl ether; 1,2-dimethoxy-ethane / 40 - 50 °C 2: 97 percent / potassium t-butoxide / diethyl ether / 16 h / 1.) ether, 16 h 3: 87 percent / NaCl, water / dimethylsulfoxide / 10 h / 150 °C 4: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 1.) Mg, iodine / 1.) THF, 0.5 h, reflux; 2.) THF, -30 deg C to RT, RT, 1 h 2: 86 percent / cc. HCl / 12 h / Heating 3: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 92 percent / piperidine, glacial acetic acid / CHCl3 / 14 h / Heating 2: 90 percent / sodium borohydride / ethanol / 0.67 h / 15 - 20 °C 3: 55 percent / Cu, pyridine / methanol / 36 h / Heating 4: 88 percent / lithium aluminium hydride / diethyl ether / Heating 5: 92 percent / pydidinum chlorochromate, celite, sodium acetate / CH2Cl2 / 5 h 6: 96 percent / diethyl ether; tetrahydrofuran / -60 °C 7: 95 percent / MnO2 / CHCl3 / 72 h / Ambient temperature 8: 97 percent / potassium t-butoxide / diethyl ether / 16 h / 1.) ether, 16 h 9: 87 percent / NaCl, water / dimethylsulfoxide / 10 h / 150 °C 10: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 96 percent / diethyl ether; tetrahydrofuran / -60 °C 2: 95 percent / MnO2 / CHCl3 / 72 h / Ambient temperature 3: 97 percent / potassium t-butoxide / diethyl ether / 16 h / 1.) ether, 16 h 4: 87 percent / NaCl, water / dimethylsulfoxide / 10 h / 150 °C 5: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 54 percent / N-bromosuccinimide, triphenylphosphine / benzene / 4 h 2: 1.) Mg, iodine / 1.) THF, 0.5 h, reflux; 2.) THF, -30 deg C to RT, RT, 1 h 3: 86 percent / cc. HCl / 12 h / Heating 4: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 91 percent / lithium aluminium hydride / diethyl ether / 4 h / Ambient temperature 2: 54 percent / N-bromosuccinimide, triphenylphosphine / benzene / 4 h 3: 1.) Mg, iodine / 1.) THF, 0.5 h, reflux; 2.) THF, -30 deg C to RT, RT, 1 h 4: 86 percent / cc. HCl / 12 h / Heating 5: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 1.) Mg, iodine / 1.) THF, 0.5 h, reflux; 2.) THF, -30 deg C to RT, RT, 1 h 2: 86 percent / cc. HCl / 12 h / Heating 3: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme

1: 92 percent / pydidinum chlorochromate, celite, sodium acetate / CH2Cl2 / 5 h 2: 96 percent / diethyl ether; tetrahydrofuran / -60 °C 3: 95 percent / MnO2 / CHCl3 / 72 h / Ambient temperature 4: 97 percent / potassium t-butoxide / diethyl ether / 16 h / 1.) ether, 16 h 5: 87 percent / NaCl, water / dimethylsulfoxide / 10 h / 150 °C 6: 98 percent / potassium t-butoxide / diethyl ether / 0.5 h / 0 °C View Scheme