oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane T=-60 - 20°C; Swern oxidation; 2 h;

1: 88 percent / NaH / tetrahydrofuran / 6 h / 20 °C 2: 100 percent / H2 / Pd/C / methanol / 4 h 3: 67 percent / LiAlH4 / tetrahydrofuran / 4 h 4: 78 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 2 h / -60 - 20 °C View Scheme

1: 100 percent / H2 / Pd/C / methanol / 4 h 2: 67 percent / LiAlH4 / tetrahydrofuran / 4 h 3: 78 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 2 h / -60 - 20 °C View Scheme

1: 67 percent / LiAlH4 / tetrahydrofuran / 4 h 2: 78 percent / oxalyl chloride; DMSO; triethylamine / CH2Cl2 / 2 h / -60 - 20 °C View Scheme