1.1: n-BuLi / tetrahydrofuran; hexane / 2 h / -50 °C 1.2: 87 percent / tetrahydrofuran; hexane / 20 h / 20 °C 2.1: 90 percent / TBAF / tetrahydrofuran / 5 h / 20 °C View Scheme

2: 100 percent / NaI / acetone / Heating 4: 83 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 5: Jones reagent / acetone / 0 °C 6: diethyl ether / 0 °C 7: 98 percent / KF*2H2O / dimethylformamide / 25 °C 8: 92 percent / n-PrNH2 / CuI, Pd(PPh3)4 / benzene / 25 °C 9: 87 percent / H2, quinoline / Lindlar catalyst / hexane / 25 °C 10: 91 percent / HF*pyridine / tetrahydrofuran / 0 - 25 °C 11: 86 percent / LiOH / tetrahydrofuran; H2O / 25 °C View Scheme