1.1: 79 percent / DIBAL / CH2Cl2; hexane / 1.5 h / -78 °C 2.1: 87 percent / zinc dust; PPh3 / CH2Cl2 / 25 °C 3.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -78 - 20 °C 3.2: 94 percent / tetrahydrofuran; hexane / -78 - 20 °C View Scheme

diisobutylaluminium hydride in hexane; dichloromethane T=-78°C; 6 h;

1: With diisobutylaluminium hydride in hexane; dichloromethane T=-110 - -90°C; 0.333333 h; Inert atmosphere; 2: With water; Potassium sodium tartrate in hexane; dichloromethane T=-90 - 20°C; Inert atmosphere;

1: 96 percent / DIBAL-H / toluene / 1.5 h / -78 °C 2: 91 percent / DBU; LiCl / acetonitrile / 19 h / 25 °C 3: 2.71 g / H2 / Pd/C / ethyl acetate / 20 h / 25 °C / 760 Torr 4: 93 percent / DIBAL-H / hexane; toluene / 2 h / 25 °C View Scheme

diisobutylaluminium hydride in diethyl ether; hexane T=-100°C; 1 h;