manganese(IV) oxide; sodium cyanide; acetic acid T=20 - 25°C; 24 h;

sodium iodide in acetone Ambient temperature;

1: 32 percent / Et3N / tetrahydrofuran; H2O / 8.5 h / 0 - 20 °C 2: 72 percent / NaCN, AcOH, MnO2 / 24 h / 20 - 25 °C View Scheme

1: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, -40 deg C, 15 min 2: 32 percent / Et3N / tetrahydrofuran; H2O / 8.5 h / 0 - 20 °C 3: 72 percent / NaCN, AcOH, MnO2 / 24 h / 20 - 25 °C View Scheme

1: K2CO3 / acetone / 18 h / Heating 2: 98 percent / LiAlH4 / tetrahydrofuran / 3.5 h / 0 - 20 °C 3: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, -40 deg C, 15 min 4: 32 percent / Et3N / tetrahydrofuran; H2O / 8.5 h / 0 - 20 °C 5: 72 percent / NaCN, AcOH, MnO2 / 24 h / 20 - 25 °C View Scheme

1: 32 percent / Et3N / tetrahydrofuran; H2O / 8.5 h / 0 - 20 °C 2: 72 percent / NaCN, AcOH, MnO2 / 24 h / 20 - 25 °C View Scheme

1: 98 percent / LiAlH4 / tetrahydrofuran / 3.5 h / 0 - 20 °C 2: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 1 h, 2.) CH2Cl2, -40 deg C, 15 min 3: 32 percent / Et3N / tetrahydrofuran; H2O / 8.5 h / 0 - 20 °C 4: 72 percent / NaCN, AcOH, MnO2 / 24 h / 20 - 25 °C View Scheme