1: With n-butyllithium in tetrahydrofuran; hexane T=-80°C; 0.75 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-80 - 20°C; 12 h; 3: With hydrogenchloride in tetrahydrofuran; hexane pH=2 - 3;

hydrogenchloride; n-butyllithium in tetrahydrofuran 1. BuLi, THF; 2. (i-PrO)3B; 3. H2O/HCl;

1.1: 95 percent / t-BuOK / tetrahydrofuran / 9 h / 0 - 20 °C 2.1: BuLi / tetrahydrofuran; hexane / 1 h / -78 °C 2.2: tetrahydrofuran; hexane / 8.5 h / -78 - 20 °C 3.1: 37.09 g / aq. HCl / 3 h View Scheme

n-butyllithium in tetrahydrofuran; cyclohexane to soln. of (C6H13)2(C13H7)Br in THF at -78°C, soln. of C4H9Li inC6H12 added dropwise; mixt. stirred at -78°C for 1 h, then (CH3O )3B added, warmed to room temp., stirred overnight, HCl added to hydrolyze for 30 min; org. layer washed with brine, dried over MgSO4, solvent removed, residuepurified by chromy. (silica gel, hexane/ethyl acetate = 2/1);

1.1: t-BuOK / dimethylformamide 2.1: BuLi; TMEDA / toluene / 2 h / 20 °C 2.2: toluene / 12 h / 20 °C 3.1: aq. HCl / 0.5 h View Scheme

1: 4-methyl-1,3-dioxolan-2-one 2: potassium hydroxide; potassium iodide / dimethyl sulfoxide 3: n-butyllithium / tetrahydrofuran View Scheme

n-butyllithium in tetrahydrofuran