1: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 2: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

1: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h 2: 82 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 3: 86 percent / Et3N / CH2Cl2 / 0.5 h / -10 - 0 °C 4: 59 percent / benzene; dimethylformamide / 16 h / Heating 5: 84 percent / H2O, NaCl / dimethylsulfoxide / 3 h / 160 - 165 °C 6: 77 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 7: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 8: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

1: 77 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 2: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 3: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

1: 84 percent / H2O, NaCl / dimethylsulfoxide / 3 h / 160 - 165 °C 2: 77 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 3: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 4: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

1: 59 percent / benzene; dimethylformamide / 16 h / Heating 2: 84 percent / H2O, NaCl / dimethylsulfoxide / 3 h / 160 - 165 °C 3: 77 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 4: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 5: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

1: 86 percent / Et3N / CH2Cl2 / 0.5 h / -10 - 0 °C 2: 59 percent / benzene; dimethylformamide / 16 h / Heating 3: 84 percent / H2O, NaCl / dimethylsulfoxide / 3 h / 160 - 165 °C 4: 77 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 5: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 6: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

1: 82 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 2: 86 percent / Et3N / CH2Cl2 / 0.5 h / -10 - 0 °C 3: 59 percent / benzene; dimethylformamide / 16 h / Heating 4: 84 percent / H2O, NaCl / dimethylsulfoxide / 3 h / 160 - 165 °C 5: 77 percent / LiAlH4, EtOH / diethyl ether / 0.5 h / 0 - 5 °C 6: 78 percent / pyridinium chlorochromate / CH2Cl2 / 4 h / 10 °C 7: 1.) NaH / 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h View Scheme

sodium hydride 1.) benzene, 5 min, 2.) benzene, 5 min; Yield given. Multistep reaction;

sodium hydride 1.) 1,2-dimethoxyethane, 20 deg C, 2.) 1,2-dimethoxyethane, 10 deg C, 4 h, 60 deg C, 1 h; Yield given. Multistep reaction;