1: 30 percent / LiAlH4 / tetrahydrofuran / 2 h / 20 °C 2: 77 percent / pyridine / 0.75 h / 20 °C 3: 12.6 mg / LiBH(Et)3 / tetrahydrofuran / 0.25 h / 20 °C 4: 73 percent / NaH / dimethylformamide / 13 h / 90 °C 5: 2.6 mg / hydrogen / Raney Ni / ethanol / 2 h / Heating View Scheme

lithium aluminium tetrahydride in tetrahydrofuran T=20°C; Elimination; deacetylation; 2 h;