zirconocene dichloride; lithium tri-t-butoxyaluminum hydride in tetrahydrofuran T=20°C; 0.0333333 h;

lanthanum trifluoromethanesulphonate 1.) Et2O, -78 deg C, 2.) 25 deg C, 20 min; Yield given. Multistep reaction;

1: 1.) tert-BuLi, TMEDA 2: acetic acid / Heating 3: BBr3 View Scheme

beryllium(II) chloride in toluene 5 h;

1: 2-methoxy-N,N-diethyl-benzamide With tert.-butyl lithium in tetrahydrofuran; pentane T=-78°C; 1.5 h; Inert atmosphere; 2: N,N-dimethyl-formamide in tetrahydrofuran; pentane T=-78°C; 3 h;

1.1: TMEDA; sec-butyllithium / hexane; tetrahydrofuran / 1 h / -78 °C 1.2: 86 percent / hexane; tetrahydrofuran / -78 - 22 °C 2.1: 65 percent / acetic acid; aq. HCl / 18 h / 120 °C View Scheme

1.1: sec.-butyllithium; N,N,N',N,-tetramethylethylenediamine / tetrahydrofuran; cyclohexane / 2 h / -78 °C / |Inert atmosphere 1.2: -78 - 20 °C / |Inert atmosphere 2.1: hydrogenchloride; acetic acid; water / 12 h / |Reflux View Scheme

Yield given. Multistep reaction;

1: 1) s-BuLi, N,N,N,N-tetramethylethylene diamine / 1) THF, cyclohexane, -78 deg C, 1 h, 2) to room temperature, 12 h 2: 1) LDA / 1) a) THF, 0 deg C, 1.5 h, b) 40-45 deg C, 0.5 h, 2) THF, 40 deg C, 12 h 3: p-toluenesulfonic acid / toluene / 12 h / Heating 4: 54 percent / BBr3 / CH2Cl2 / a) -78 deg C, 1 h, b) without cooling, 20 h View Scheme

1.1: s-BuLi; TMEDA / tetrahydrofuran; cyclohexane / 1 h / -78 °C 1.2: tetrahydrofuran; cyclohexane / -78 - 20 °C 1.3: 97 percent / aq. HCl; NH4Cl / tetrahydrofuran; cyclohexane / pH 5 - 6 2.1: 85 percent / Pd(PPh3)4; aq. Na2CO3 / 1,2-dimethoxy-ethane / Heating 3.1: 92 percent / LDA / tetrahydrofuran / 3 h / 20 °C 4.1: n-BuLi / diethyl ether; hexane / 0.08 h / 0 °C 4.2: 75 percent / diethyl ether; hexane / 0 - 20 °C 5.1: 97 percent / aq. HCO2H; Pd(OAc)2; Ph3P / dimethylformamide / 60 - 70 °C View Scheme