sulfuric acid in tetrahydrofuran 0.5 h; Ambient temperature;

1: With sodium hydride in ethylene glycol dimethyl ether T=20°C; 0.5 h; 2: With lithium aluminium tetrahydride in ethylene glycol dimethyl ether 3 h; Heating; Further stages.;

sec-butylmagnesium chloride; copper(l) chloride in diethyl ether 1) -20 deg C, 2) RT, 3d;

1: 1.) n-butyllithium, tetramethylethylenediamine / 1a.) ether, 0 deg C, 30 min, 1b.) ether/THF, RT, 48 h, 2a.) -45 deg C, 10 min, 2b.) RT, 20 min 2: 93 percent / aq. 1N H2SO4 / tetrahydrofuran / 0.5 h / Ambient temperature View Scheme