1: 100 percent / NaI / acetone / Heating 3: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 4: Jones reagent / acetone / 0 °C 5: diethyl ether / 0 °C 6: 98 percent / KF*2H2O / dimethylformamide / 25 °C 7: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 8: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 9: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 10: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme

With  sodium iodide in  acetone  Heating;   

Multi-step reaction with 5 steps 1: 100 percent / NaI / acetone / Heating3: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C4: Jones reagent / acetone / 0 °C5: diethyl ether / 0 °C  

Multi-step reaction with 6 steps 1: 100 percent / NaI / acetone / Heating3: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C4: Jones reagent / acetone / 0 °C5: diethyl ether / 0 °C6: 98 percent / KF*2H2O / dimethylformamide / 25 °C  

Multi-step reaction with 7 steps 1: 100 percent / NaI / acetone / Heating3: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C4: Jones reagent / acetone / 0 °C5: diethyl ether / 0 °C6: 98 percent / KF*2H2O / dimethylformamide / 25 °C7: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C  

Multi-step reaction with 3 steps 1: 100 percent / NaI / acetone / Heating3: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C