1: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 2: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C View Scheme

1: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 2: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C 3: 72 percent / Ag2O; MnO2; aq. NaOH / methanol / 2 h / 60 °C View Scheme

methanol; methyllithium; tert.-butyl lithium in tetrahydrofuran; diethyl ether; pentane T=-78°C; desulfuration; 0.166667 h; rate of RLi addition is 2.1 mL/h;

1: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 2: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C 3: 72 percent / Ag2O; MnO2; aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 2: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C 3: 72 percent / Ag2O; MnO2; aq. NaOH / methanol / 2 h / 60 °C View Scheme