1.1: TMEDA / diethyl ether; pentane / 0.5 h / 20 °C 2.1: TMEDA; n-BuLi / 1 h / -78 °C 2.2: 1 h / -78 °C 2.3: 0.119 g / NaOH / ethanol / 2 h / 20 °C View Scheme

1.1: TMEDA / diethyl ether; pentane / 0.5 h / 20 °C 2.1: n-butyllithium; TMEDA / diethyl ether; pentane / 1 h / -78 °C 2.2: I2 / diethyl ether; pentane / 1 h / -78 °C 3.1: 0.281 g / aq. HCl / methanol / -78 - 20 °C 4.1: 97 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: TMEDA / diethyl ether; pentane / 0.5 h / 20 °C 2.1: n-butyllithium; TMEDA / diethyl ether; pentane / 1 h / -78 °C 2.2: C2Cl6 / diethyl ether; pentane / 1 h / -78 °C 3.1: 0.210 g / aq. HCl / methanol / -78 - 20 °C 4.1: 98 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C View Scheme

1.1: TMEDA / diethyl ether; pentane / 0.5 h / 20 °C 2.1: n-butyllithium; TMEDA / diethyl ether; pentane / 1 h / -78 °C 2.2: BrCH2CH2Br / diethyl ether; pentane / 1 h / -78 °C 3.1: 0.248 g / aq. HCl / methanol / -78 - 20 °C 4.1: 98 percent / aq. NaOH / ethanol; tetrahydrofuran / 2 h / 20 °C View Scheme