sodium cyanoborohydride; zinc(II) iodide in 1,2-dichloro-ethane 20 h; Heating;

boron trifluoride diethyl etherate; sodium cyanoborohydride in tetrahydrofuran 10 h; Heating;

1: 70 percent / K2CO3 / dimethylformamide / 72 h / Ambient temperature 2: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, 100 deg C, 4 5 min, 2.) diethylene glycol, 150 deg C, 3 h View Scheme

1: 72 percent / Br2, AcOH / 12 h / Ambient temperature 2: 70 percent / K2CO3 / dimethylformamide / 72 h / Ambient temperature 3: 1.) hydrazine hydrate, 2.) KOH / 1.) diethylene glycol, 100 deg C, 4 5 min, 2.) diethylene glycol, 150 deg C, 3 h View Scheme

copper(l) chloride in methanol; N,N-dimethyl-formamide T=140°C; 8 h; Autoclave; TemperatureTime;

1: bromine / 1,2-dichloro-ethane / 7 h / 20 - 25 °C 2: sodium hydroxide / water; 1,2-dichloro-ethane / 5 h / 30 - 35 °C 3: copper(l) chloride / methanol; N,N-dimethyl-formamide / 8 h / 140 °C / |Autoclave View Scheme

1: sodium hydroxide / water; 1,2-dichloro-ethane / 5 h / 30 - 35 °C 2: copper(l) chloride / methanol; N,N-dimethyl-formamide / 8 h / 140 °C / |Autoclave View Scheme

potassium hydroxide

1: 16 percent / lithium / tetrahydrofuran / 1 h / sonication 2: 90 percent / PCC; silica gel / CH2Cl2 / 3 h / 20 °C 3: 90 percent / tetrahydrofuran / 2 h / sonication 4: 97 percent / hydrogen / Pd-CaCO3 / ethanol / 24 h / 20 °C 5: 85 percent / PCC; silica gel / CH2Cl2 / 30 h / 20 °C 6: 75 percent / sodium borohydride / methanol / 1.5 h / cooling 7: 28 percent / propionic acid / 48 h / 180 °C 8: 80 percent / Cl2(PCy3)2Ru=CHPh / CH2Cl2 / 6 h / 20 °C 9: 99 percent / hydrogen / Pd on activated C / ethanol / 3 h / 20 °C / 760 Torr 10: 98 percent / LiAlH4 / diethyl ether / 1 h / 0 °C 11: 89 percent / PCC; silica gel / CH2Cl2 / 0.5 h / 20 °C 12: 77 percent Turnov. / (Ph3P)3RhCl / benzene / 20 h / 120 - 130 °C View Scheme