potassium hydroxide; sodium dithionite in methanol 1 h; Ambient temperature;

1: 10 percent KOH / ethanol / 0.17 h / 50 °C 2: 1.) 60 percent NaH oil dispersion / 1.) DMF, 0 deg C, 15 min, 2.) 0 deg C to RT, 3 h at RT 3: 1.) n-BuLi / 1.) THF, tetramethylethylenediamine, hexane, 0 to 20 deg C; 2.) THF, RT, 1 h 4: Lithium / tetrahydrofuran; liquid ammonia / -30 °C / large excess of lithium 5: 93 percent / 48 percent HBr / ethanol / 0.25 h / 65 °C 6: 81 percent / O2 / salcomine / dimethylformamide / 3 h / Ambient temperature 7: 77 percent / 70 percent HClO4 / CH2Cl2 / 1 h / Ambient temperature View Scheme