n-butyllithium in tetrahydrofuran T=-78°C; 0.166667 h;

1: 64 percent / BuLi / hexane; tetrahydrofuran / 2.5 h / -78 °C 2: 67 percent / pyridinium toluene-p-sulphonate / tetrahydrofuran; H2O / 3 h / Ambient temperature 3: 67 percent / diethyl ether / 2 h / Ambient temperature 4: 97 percent / toluene-p-sulphonic acid / toluene / 5.5 h / Heating View Scheme

triethylamine in dichloromethane 2 h; Ambient temperature;

1: 70 percent / PPh3, Et3N, PdCl2, CuI / dimethylformamide / 8 h / 80 °C 2: H2 / Raney Ni / methanol / 20 °C 3: 85 percent / TsOH*H2O / toluene / Heating View Scheme

1: 70 percent / PPh3, Et3N, PdCl2, CuI / dimethylformamide / 8 h / 80 °C 2: H2 / Raney Ni / methanol / 20 °C 3: K2CO3 / acetone / 70 °C 4: 75 percent / TsOH*H2O / toluene / Heating 5: 5percent aq. NaOH / methanol / 50 °C 6: DDQ / benzene / 80 °C View Scheme

1: 70 percent / PPh3, Et3N, PdCl2, CuI / dimethylformamide / 8 h / 80 °C 2: H2 / Raney Ni / methanol / 20 °C View Scheme