triethylamine in dichloromethane

1: (i) LDA, CuI, (ii) /BRN= 1633479/, (iii) LiAlH4, Et2O 2: Et3N / CH2Cl2 View Scheme

1: 91 percent / LiAlH4 / diethyl ether / 10 h / 0 °C 2: Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

1: 1.) NaH, (iPr)2NH, 2.) n-BuLi / 1.) THF, 0 deg C and reflux, 15 min, 2.) THF, HMPA, 0 deg C, 15 min and 35 deg C 30 min, 3.) THF, HMPA, 0 deg C and 3 h, 25 deg C 2: 91 percent / LiAlH4 / diethyl ether / 10 h / 0 °C 3: Et3N / CH2Cl2 / 1 h / 0 °C View Scheme

1: 70 percent / NaCl, H2O / dimethylsulfoxide / 12 h / 180 °C 2: 86 percent / LAH / tetrahydrofuran / 1 h / Ambient temperature 3: triethylamine / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 30 min View Scheme

1: 86 percent / LAH / tetrahydrofuran / 1 h / Ambient temperature 2: triethylamine / tetrahydrofuran / 1.) 0 deg C, 30 min, 2.) room temperature, 30 min View Scheme

sodium iodide in acetone