1: 98 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -35 deg C, 30 min, 2.) -30 deg C, 3 h 2: 66 percent / conc. hydrochloric acid / 0.08 h / Heating 3: 76.7 percent / sodium borohydride / ethanol / Ambient temperature View Scheme

1: 98 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -35 deg C, 30 min, 2.) -30 deg C, 3 h 2: 90 percent / conc. hydrochloric acud / Heating 3: 68 percent / 1.) 10 percent acetic acid, sodium acetate, 2.) NaI / 0.25 h / Heating View Scheme

1: 98 percent / n-BuLi / tetrahydrofuran; hexane / 1.) -35 deg C, 30 min, 2.) -30 deg C, 3 h 2: 66 percent / conc. hydrochloric acid / 0.08 h / Heating 3: 76.7 percent / sodium borohydride / ethanol / Ambient temperature 4: 95 percent / iodine, potassium acetate / methanol / Heating View Scheme