diisobutylaluminium hydride in hexane; dichloromethane T=-78°C; 1 h;

1: 84 percent / Pd(PPh3)4 / tetrahydrofuran / 1 h / 20 °C 2: 80 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C View Scheme

1: acetonitrile / 13 h / 20 °C 2: 1.015 g / γ-collidine / CH2Cl2 / 1 h / -78 °C 3: 89 percent / DIBAL / CH2Cl2; hexane / 1 h / -78 °C 4: 93 percent / MsCl; LiCl; 2,6-lutidine / dimethylformamide / 2 h / -5 °C 5: 98 percent / TBAF / tetrahydrofuran / 3 h / 20 °C View Scheme