1: 61 percent / Et3N / tetrahydrofuran / -78 - 25 °C 2: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 3: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C View Scheme

1: 61 percent / Et3N / tetrahydrofuran / -78 - 25 °C 2: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 3: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C 4: 72 percent / Ag2O; MnO2; aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 61 percent / Et3N / tetrahydrofuran / -78 - 25 °C 2: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h View Scheme

1: 61 percent / Et3N / tetrahydrofuran / -78 - 25 °C 2: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 3: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C 4: 72 percent / Ag2O; MnO2; aq. NaOH / methanol / 2 h / 60 °C View Scheme

1: 61 percent / Et3N / tetrahydrofuran / -78 - 25 °C 2: 67 percent / MeLi; t-BuLi; MeOH / tetrahydrofuran; diethyl ether; pentane / 0.17 h / -78 °C / rate of RLi addition is 2.1 mL/h 3: 93 percent / Bu4NF / tetrahydrofuran / 1.5 h / 25 °C 4: 72 percent / Ag2O; MnO2; aq. NaOH / methanol / 2 h / 60 °C View Scheme

triethylamine in tetrahydrofuran T=-78 - 25°C; Addition; isomerization;

triethylamine in tetrahydrofuran T=-78 - 25°C; Addition; isomerization;