oxalyl dichloride; dimethyl sulfoxide; triethylamine in dichloromethane T=-78 - 20°C; Swern oxidation;

1: 1.) Na / 1.) anhydrous Et2O, 0-5 deg C, 2.) abs. ethanol, 0 deg C, 6h, 3.) RT, 4.) abs. ethanol, 1h 2: 65 percent / H2 / Raney nickel / ethanol / 760 Torr / Ambient temperature 3: 24 percent / p-TsOH monohydrate / toluene / 3 h / Heating View Scheme

1: 65 percent / H2 / Raney nickel / ethanol / 760 Torr / Ambient temperature 2: 24 percent / p-TsOH monohydrate / toluene / 3 h / Heating View Scheme

toluene-4-sulfonic acid in toluene 3 h; Heating;

1.1: LDA / tetrahydrofuran; hexane / 0.83 h / -78 °C 1.2: 94 percent / tetrahydrofuran; hexane / 0.17 h / -78 °C 2.1: 84 percent / (COCl)2; DMSO; Et3N / CH2Cl2 / -78 - 20 °C View Scheme