1: 2.14 M n-BuLi / tetrahydrofuran; hexane / -35 °C 2: 383 mg / NaCNBH3 / methanol; acetic acid / 0.25 h 3: 66 percent / conc. hydrochloric acid / 0.08 h / Heating 4: 76.7 percent / sodium borohydride / ethanol / Ambient temperature View Scheme

1: 2.14 M n-BuLi / tetrahydrofuran; hexane / -35 °C 2: 383 mg / NaCNBH3 / methanol; acetic acid / 0.25 h 3: 90 percent / conc. hydrochloric acud / Heating 4: 68 percent / 1.) 10 percent acetic acid, sodium acetate, 2.) NaI / 0.25 h / Heating View Scheme

1: 2.14 M n-BuLi / tetrahydrofuran; hexane / -35 °C 2: 383 mg / NaCNBH3 / methanol; acetic acid / 0.25 h 3: 66 percent / conc. hydrochloric acid / 0.08 h / Heating 4: 76.7 percent / sodium borohydride / ethanol / Ambient temperature 5: 95 percent / iodine, potassium acetate / methanol / Heating View Scheme