magnesium bromide in diethyl ether; benzene T=-78 - 25°C; 0.5 h;

1: 1.) LiAlH4, 2.) (COCl)2, NEt3 / 1.) diethyl ether, 0 deg C, 2.) diethyl ether, DMSO 2: 72 percent / MgBr2 / diethyl ether View Scheme

1: 95 percent / pyridine / tetrahydrofuran / 2 h / 0 °C 2: 1.) LDA / 1.) THF, -78 deg C, 1.5 min, 2.) THF, -78 deg C, 10 min 3: tetrahydrofuran / 2 h / -78 - 25 °C 4: LiAlH4 / tetrahydrofuran / 0 °C 5: 99 percent / (COCl)2, (CH3)2SO, (C2H5)3N / CH2Cl2 / 1 h / Ambient temperature 6: 72 percent / MgBr2*Et2O / diethyl ether; benzene / 0.5 h / -78 - 25 °C View Scheme

1: 1.) LDA / 1.) THF, -78 deg C, 1.5 min, 2.) THF, -78 deg C, 10 min 2: tetrahydrofuran / 2 h / -78 - 25 °C 3: LiAlH4 / tetrahydrofuran / 0 °C 4: 99 percent / (COCl)2, (CH3)2SO, (C2H5)3N / CH2Cl2 / 1 h / Ambient temperature 5: 72 percent / MgBr2*Et2O / diethyl ether; benzene / 0.5 h / -78 - 25 °C View Scheme