2: 1) NaOEt, 2) NaH / 1) reflux, 6 h, 2) toluene, reflux, 40 h 3: 1) NaoH, 2) HCl / ethanol / 24 h / Heating 4: 1.42 h / 160 °C 5: 69 percent / 0.38 N HCl / 1 h / Ambient temperature 6: 1) Ag2O, MeOH, 2) Br2, 3) Zn / 2) CCl4, 3) HOAc, reflux, 2 h 7: alkalin View Scheme

1: 10 percent / Et3N / diethyl ether / 0.5 h / Ambient temperature 2: 84.4 percent / NaBH4, NaH, 2-propanol / dioxane / 1.) 70 deg C, 2.) reflux, 1 h View Scheme

(i) Et3N, (ii) NaH, NaBH4, iPrOH; Multistep reaction;

pyridine in dichloromethane T=0 - 20°C; 17.5 h;

2,3-dimethyl aniline T=20°C;

benzoylchlorobis(triphenylphosphine)palladium(II) in chloroform T=65°C; 5 h;

aluminium trichloride in N,N-dimethyl-formamide T=90°C; 1 h; Yield given;

diethyl ether; phenyl-Cd-phenyl

1: AlCl3 / dimethylformamide / 1 h / 90 °C 2: 85 percent / dimethylsulfoxide / 2 h / 80 °C 3: 95 percent / NH2NH2*H2O, KOH / bis-(2-hydroxy-ethyl) ether / 4 h / Heating 4: 95 percent / diethyl ether / 12 h / 0 °C 5: 90 percent / LiAlH4 / diethyl ether / 4 h / Heating 6: 88 percent / Me3SiI / CH2Cl2 / 24 h / Ambient temperature 7: 1.) n-BuLi / 1.) THF, -78 deg C, 2.) THF, a) -78 deg C, 10 min, b) from -78 deg C to RT 8: 86 percent / concd H2SO4 / 24 h / Heating 9: 1.) Tl(OCOCF3)3, 2.) aq. KI / 1.) TFA, RT, 5 d, 2.) TFA, 15 min 10: 90 percent / 1 N NaOH / ethanol / 1.5 h / Heating View Scheme

triethylamine in dichloromethane 12 h; Heating;