1,1'-carbonyldiimidazole in tetrahydrofuran; diethyl ether T=20°C; 4 h;

1: oxalyl chloride / benzene / 10 - 20 °C 2: 77 percent / aq. ammonia / tetrahydrofuran / 6 h / 0 °C 3: LiAlH4 / tetrahydrofuran / 0 - 20 °C 4: 67 percent / 1,1'-carbonyldiimidazole / tetrahydrofuran; diethyl ether / 4 h / 20 °C View Scheme

1: LiAlH4 / tetrahydrofuran / 0 - 20 °C 2: 67 percent / 1,1'-carbonyldiimidazole / tetrahydrofuran; diethyl ether / 4 h / 20 °C View Scheme

1: 77 percent / aq. ammonia / tetrahydrofuran / 6 h / 0 °C 2: LiAlH4 / tetrahydrofuran / 0 - 20 °C 3: 67 percent / 1,1'-carbonyldiimidazole / tetrahydrofuran; diethyl ether / 4 h / 20 °C View Scheme

1: 69 percent / lithium aluminium hydride / diethyl ether / 2 h 2: sodium hydroxide / H2O View Scheme

sodium hydroxide in water