1.1: n-BuLi / tetrahydrofuran; hexane / 0.33 h / -78 °C 1.2: tetrahydrofuran; hexane / 3.5 h / -78 - 20 °C 2.1: NaH / tetrahydrofuran / 3.5 h / 0 - 20 °C 3.1: H2; quinoline / Lindlar catalyst / ethyl acetate / 20 °C / 760 Torr 4.1: p-TsOH / methanol / 16 h / 20 °C 5.1: n-Bu4NBr; aq. NaOH / benzene / 18 h / 20 °C 6.1: 91 percent / n-BuLi / diethyl ether; hexane / -40 - -20 °C 7.1: 82 percent / o-xylene / 8 h / Heating View Scheme

in o-xylene Claisen-Cope tandem rearrangement; 8 h; Heating;

1: n-Bu4NBr; aq. NaOH / benzene / 18 h / 20 °C 2: 91 percent / n-BuLi / diethyl ether; hexane / -40 - -20 °C 3: 82 percent / o-xylene / 8 h / Heating View Scheme

1: 91 percent / n-BuLi / diethyl ether; hexane / -40 - -20 °C 2: 82 percent / o-xylene / 8 h / Heating View Scheme