titanium tetrachloride; zinc in tetrahydrofuran; dichloromethane T=18 - 20°C; 12 h;

lithium; tert-butyl alcohol in diethyl ether 2 h; Heating;

1: 45 percent / aq. 50percent NaOH / triethylbenzylammonium hydroxide / pentane / 1.) room temperature, 3 h, 2.) 40 deg C, 5 h; 2: 60 percent / Li, tert-butyl alcohol / diethyl ether / 2 h / Heating View Scheme

1: 52 percent / Zn dust, TiCl4 / tetrahydrofuran; CH2Cl2 / 12 h / 18 - 20 °C 2: 45 percent / aq. 50percent NaOH / triethylbenzylammonium hydroxide / pentane / 1.) room temperature, 3 h, 2.) 40 deg C, 5 h; 3: 60 percent / Li, tert-butyl alcohol / diethyl ether / 2 h / Heating View Scheme