1: 1.) NaH / 1.) THF, 1 h, 2.) RT, 1 h 2: 1.) bora-9 bicyclo <3,3,1> nonane, 2.) 30percent H2O2, 3M NaOH / 1.) THF, 1 h, 2.) THF, reflux, 3 h 3: 2N HCl / H2O / 12 h / Heating View Scheme

(i) aq. NaOH, <nBu4N>HSO4, (ii) HCl; Multistep reaction;

1.1: s-BuLi; i-Pr2NH / cyclohexane; tetrahydrofuran / 0.17 h / -78 °C 1.2: 78 percent / tetrahydrofuran / 16 h / -78 - 20 °C 2.1: s-BuLi; TMEDA / cyclohexane; diethyl ether / 0.5 h / -78 °C 2.2: 77 percent / AcOH / diethyl ether 3.1: 6 M HCl / 16 h / Heating 3.2: Dowex 50W,H+ View Scheme

(i) aq. NaOH, <nBu4N>HSO4, (ii) HCl; Multistep reaction;

tetrabutylammomium bromide; sodium hydride benzene, 1.) 50 deg C, 2 h, 2.) reflux, 2 h, then 20-25 deg C, overnight; Yield given. Multistep reaction;

1.1: LDA / cyclohexane; tetrahydrofuran / 0.17 h / -78 °C 1.2: 72 percent / tetrahydrofuran / 16 h / -78 - 20 °C 2.1: s-BuLi; TMEDA / cyclohexane; diethyl ether / 0.5 h / -78 °C 2.2: 70 percent / AcOH / diethyl ether View Scheme