potassium fluoride in dimethyl sulfoxide T=150°C; 3 h;

1: 80 percent / 1.) DIBAH, 2.) pyridine, 3.) bromine / diethyl ether; CH2Cl2 / 1.) 5 to 40 deg C, 3.5 h, 2.) 0 deg C, 3.) -78 deg C 2: 78 percent / 1.) sec-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 4 min, 2.) -78 deg C to RT, 2 h 3: 61 percent / anhydr. KF / dimethylsulfoxide / 3 h / 150 °C View Scheme

1: 78 percent / 1.) sec-BuLi / tetrahydrofuran; cyclohexane / 1.) -78 deg C, 4 min, 2.) -78 deg C to RT, 2 h 2: 61 percent / anhydr. KF / dimethylsulfoxide / 3 h / 150 °C View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 3 h; Heating;

1.1: n-BuLi / tetrahydrofuran; hexane / 0.25 h / 0 °C 1.2: tetrahydrofuran / 1 h / -30 - -20 °C / 20 deg C, 2 h 2.1: LiAlH4 / tetrahydrofuran / 3 h / Heating View Scheme