1: 62 percent / t-BuMgCl / diethyl ether; tetrahydrofuran / 3 h / 0 °C 2: 100 percent / n-Bu4NF / tetrahydrofuran / 0.5 h / 0 °C 3: 1.) Na, liq. NH3, 2.) KMnO4, acetic acid, Adogen 464 / 1.) Et2O, -78 deg C, 30 min, 2.) CH2Cl2, H2O, reflux 4: 84 percent / acetonitrile; acetic acid / Kolbe-type electrolysis, Pt electrodes, undivided cell View Scheme

With  tetrabutyl ammonium fluoride; copper trifluoromethanesulfonate; calcium carbonate  1.) dioxane, reflux, 0.2 h;  Yield given. Multistep reaction;   

With  1,1-dimethylethylmagnesium chloride in  tetrahydrofuran; diethyl ether T=0°C; 3 h;