1: 92 percent / 57 percent NaH / dimethylsulfoxide; paraffin / 1.) 75 deg C; 2.) 60 deg C, 3 h 2: 83 percent / conc. HCl / acetone / 4.5 h / Ambient temperature 3: 91 percent / BF3*Et2O / tetrahydrofuran / 2.75 h / Heating 4: t-BuOK / tetrahydrofuran / 2 h / -20 - -15 °C 5: 58 percent / Na / liquid ammonia; tetrahydrofuran / 1 h / -4 °C View Scheme

1: 1.) NaH / 1.) DMSO, 70 deg C, 1.5 h, 2.) 60 deg C, 5 h 2: 86 percent / conc. HCl / 5 h / Ambient temperature View Scheme