hydrogen; nickel in ethanol Heating;

1: 98 percent / H2 / 10percent Pd/C / ethyl acetate / 5 h / 2585.7 Torr / Ambient temperature 2: 89 percent / ammonium acetate, acetic acid / toluene / Heating 3: ethanol; H2O / 5 h / Heating 4: acetic acid, hydrochloric acid, H2O / 84 h / Heating 5: 89 percent / acetic anhydride / 4 h / Heating 6: Heating 7: LiAlH4 / diethyl ether / 3 h View Scheme

1.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran 2.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C 2.2: tetrahydrofuran 3.1: 93 percent / LiAlH4 / tetrahydrofuran / Heating 4.1: 95 percent / aq. HCl 5.1: 42 percent / BF3*OEt2 / 90 °C 6.1: 39 percent / hydrogen / Raney nickel / ethanol / Heating 7.1: 64 percent / BF3*OEt2 / 90 °C 8.1: 43 percent / hydrogen / Raney nickel / ethanol / Heating View Scheme

1.1: t-BuLi; HMPA / tetrahydrofuran / -78 °C 1.2: tetrahydrofuran 2.1: 93 percent / LiAlH4 / tetrahydrofuran / Heating 3.1: 95 percent / aq. HCl 4.1: 42 percent / BF3*OEt2 / 90 °C 5.1: 39 percent / hydrogen / Raney nickel / ethanol / Heating 6.1: 64 percent / BF3*OEt2 / 90 °C 7.1: 43 percent / hydrogen / Raney nickel / ethanol / Heating View Scheme

1: 95 percent / aq. HCl 2: 42 percent / BF3*OEt2 / 90 °C 3: 39 percent / hydrogen / Raney nickel / ethanol / Heating 4: 64 percent / BF3*OEt2 / 90 °C 5: 43 percent / hydrogen / Raney nickel / ethanol / Heating View Scheme

1: 64 percent / BF3*OEt2 / 90 °C 2: 43 percent / hydrogen / Raney nickel / ethanol / Heating View Scheme

1: 42 percent / BF3*OEt2 / 90 °C 2: 39 percent / hydrogen / Raney nickel / ethanol / Heating 3: 64 percent / BF3*OEt2 / 90 °C 4: 43 percent / hydrogen / Raney nickel / ethanol / Heating View Scheme

1: 89 percent / ammonium acetate, acetic acid / toluene / Heating 2: ethanol; H2O / 5 h / Heating 3: acetic acid, hydrochloric acid, H2O / 84 h / Heating 4: 89 percent / acetic anhydride / 4 h / Heating 5: Heating 6: LiAlH4 / diethyl ether / 3 h View Scheme

1: ethanol; H2O / 5 h / Heating 2: acetic acid, hydrochloric acid, H2O / 84 h / Heating 3: 89 percent / acetic anhydride / 4 h / Heating 4: Heating 5: LiAlH4 / diethyl ether / 3 h View Scheme

1: 89 percent / acetic anhydride / 4 h / Heating 2: Heating 3: LiAlH4 / diethyl ether / 3 h View Scheme