1: 1,5-dihydroxypentane With sodium hydride in tetrahydrofuran T=20°C; 0.5 h; 2: triisopropylsilyl chloride in tetrahydrofuran T=0°C; 0.666667 h;

1: 73 percent / IBX 2: 64 percent / HMDS; n-BuLi; I2 / tetrahydrofuran / 0.17 h / -78 °C View Scheme