1: With n-butyllithium in tetrahydrofuran; hexane T=-78°C; 1.25 h; 2: With tri-isopropoxy-borane in tetrahydrofuran; hexane T=-78°C; 1.5 h;

n-butyllithium in tetrahydrofuran; hexane; ethyl acetate

1.1: 99 percent / K2CO3 / acetone / 8 h / 65 °C 2.1: N-BuLi / tetrahydrofuran; hexane / 1.25 h / -78 °C 2.2: 83 percent / triisopropyl borate / tetrahydrofuran; hexane / 1 h / -78 °C View Scheme

CH3CH2CH2CH2Li in tetrahydrofuran; hexane (Ar); addn. of 2.5 M soln. of butyllithium in hexanes to THF soln. of manisyl bromide at -78°C, stirring for 20 min at -78°C, addn. of boron compd., stirring overnight at room temp.; quenching with aq. HCl and water, stirring for 6 h at room temp., addn. of diethyl ether, washing with water, separating organic layer, drying over MgSO4, filtration, evapn., NMR and HRMS;

1: With lithium aluminium tetrahydride in tetrahydrofuran T=0 - 20°C; 3 h; Inert atmosphere; 2: With Glauber's salt; sulfuric acid in tetrahydrofuran; water