1: 73 percent / LiAlH4 / tetrahydrofuran / -70 to -30 deg C 2: 91 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT 3: 60 percent / NEt3, NaI / acetonitrile / 15 h / 85 °C 4: 80 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 5: TsOH / tetrahydrofuran; H2O / 0.17 h 6: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 7: 92 percent / LiOH / tetrahydrofuran / 15 h / Ambient temperature View Scheme

1: 73 percent / LiAlH4 / tetrahydrofuran / -70 to -30 deg C 2: 91 percent / Ph3PBr2, pyridine / acetonitrile / 1 h / 0 deg C to RT 3: 60 percent / NEt3, NaI / acetonitrile / 15 h / 85 °C 4: 80 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT 5: TsOH / tetrahydrofuran; H2O / 0.17 h 6: 50 percent / NaN(SiMe3)2 / tetrahydrofuran / -100 deg C to RT View Scheme