1: acetonitrile / 24 h / Heating 2: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 3: 100 percent / H+ / tetrahydrofuran 4: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C 5: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 6: 95 percent / acetonitrile / Heating 7: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C 8: 92 percent / LiOH / tetrahydrofuran; H2O View Scheme

1: acetonitrile / 24 h / Heating 2: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 3: 100 percent / H+ / tetrahydrofuran 4: 60 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 1 h, 2.) -90 deg C 5: 93 percent / LiOH / tetrahydrofuran; H2O View Scheme

1: acetonitrile / 24 h / Heating 2: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 3: 100 percent / H+ / tetrahydrofuran 4: 86 percent / LiAlH4 / tetrahydrofuran / -70 °C 5: 94 percent / CBr4, Ph3P / CH2Cl2 / 1.) 0 deg C, 15 min, 2.) room temperature, 1 h 6: 95 percent / acetonitrile / Heating 7: 76 percent / NaN(SiMe3)2 / tetrahydrofuran / -80 °C View Scheme

1: acetonitrile / 24 h / Heating 2: 56 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 2.) -90 deg C 3: 100 percent / H+ / tetrahydrofuran 4: 60 percent / NaN(SiMe3)2 / tetrahydrofuran / 1.) room temperature, 1 h, 2.) -90 deg C View Scheme

ethanol