1: NaI / acetonitrile / 12 h / 20 °C 2: 21.52 g / NaBH4 / dimethylsulfoxide / 12 h / 20 °C View Scheme

pyridinium chlorochromate in dichloromethane T=20°C; 2 h;

1.1: NaI / acetonitrile / 12 h / 20 °C 2.1: 21.52 g / NaBH4 / dimethylsulfoxide / 12 h / 20 °C 3.1: n-BuLi / hexane; tetrahydrofuran / 1 h / -78 °C 3.2: 93 percent / hexane; tetrahydrofuran / -78 - 20 °C View Scheme