1: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 2: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 3: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 4: 52 percent / CuI / tetrahydrofuran / -26 °C 5: 89 percent / aq. HCl / methanol / 44 h / 20 °C View Scheme

1: 99 percent / LiAlH4 / tetrahydrofuran / 0 °C 2: 98 percent / HF; pyridine / acetonitrile / 1 h / 20 °C 3: 80 percent / N-bromosuccinimide; triphenylphosphine / CH2Cl2 4: 52 percent / CuI / tetrahydrofuran / -26 °C 5: 89 percent / aq. HCl / methanol / 44 h / 20 °C 6: 18 percent / H2 / Wilkinson's catalyst / ethanol View Scheme