sodium hydroxide in methanol T=20°C; 3 h;

1: 81.9 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 2: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 3: p-toluenesulfonic acid / methanol / 1 h / 20 °C 4: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 5: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 6: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 2: p-toluenesulfonic acid / methanol / 1 h / 20 °C 3: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 4: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 5: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 2: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 3: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: (i) EtMgBr, THF, (ii) /BRN= 1744118/, CuCl 2: (i) EtMgBr, THF, (ii) /BRN= 1908795/, CuCN View Scheme

tetrahydrofuran; ethylmagnesium bromide anschliessend mit 1-Brom-tetradeca-2,5,8-triin und Kupfer(I)-cyanid;

1: K2CO3, NaI, CuI / dimethylformamide / 4 h / 20 °C 2: K2CO3 / methanol / 4 h / 20 °C 3: 81.9 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 4: K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 5: p-toluenesulfonic acid / methanol / 1 h / 20 °C 6: 79.2 percent / PPh3, CBr4 / CH2Cl2 / 0.67 h / 0 °C 7: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 8: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: 75.5 percent / gaseous HCl / methanol; H2O / 6 h / 60 °C 2: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 3: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 2: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme

1: 0.89 g / K2CO3, NaI, CuI / dimethylformamide / 5 h / 20 °C 2: 66.3 percent / 5percent aq. NaOH / methanol / 3 h / 20 °C View Scheme