1: 71 percent / (Et2AlH2)Na / toluene; tetrahydrofuran 2: 74 percent / Et3N / benzene 3: 84 percent / benzene / 1 h / Ambient temperature 4: 91 percent / H2 / 10percent Pd-C / ethanol 5: 62 percent / PPA / xylene; CHCl3 / 100 °C 6: NaBH4 / ethanol 7: 71 percent / 10percent H2SO4 / H2O / Heating 8: 91 percent / H2 / 10 percent Pd-C / ethanol View Scheme

1: 95 percent / n-BuLi / tetrahydrofuran / -60 °C 2: 90 percent / (Et2AlH2)Na / toluene; tetrahydrofuran 3: 75 percent / Et3N / benzene 4: 83 percent / benzene 5: 75 percent / KOH / ethanol / Heating View Scheme