1.1: butyllithium; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran / 0.25 h / -75 °C 1.2: methanol 2.1: 92 percent / aq. sodium hydroxide; zinc powder / 6 h / 25 °C View Scheme

1: With 2,2,6,6-tetramethyl-piperidine; n-butyllithium in tetrahydrofuran T=-75°C; 0.25 h; 2: With methanol

1.1: butyllithium; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran / 0.25 h / -75 °C 1.2: methanol 2.1: 2 equiv. butyllithium / toluene; hexane / 1 h / -75 °C 2.2: 71 percent / toluene; hexane View Scheme

1.1: butyllithium; 2,2,6,6-tetramethylpiperidine / tetrahydrofuran / 0.25 h / -75 °C 1.2: methanol 2.1: isopropylmagnesium chloride / tetrahydrofuran / 2 h / 0 °C 2.2: 59 percent / iodine / tetrahydrofuran / 1 h / -75 °C View Scheme