1: 1) CH3Li*LiBr / 1) THF, RT, 3.5 h, 2) THF, HMPA, RT, 30 min 2: KF*2H2O / dimethylformamide / 0.5 h / Ambient temperature 3: 1) n-butyllithium / 1) THF, -23 deg C, 1 h, 2) THF, HMPA, 2.1) -23 deg C, 30 min., 2.2) RT, 1.5 h 4: 91 percent / 37percent HCl / methanol / Ambient temperature 5: 86 percent / pyridinium dichromate / dimethylformamide / Ambient temperature View Scheme

1: 1) CH3Li*LiBr / 1) THF, RT, 3.5 h, 2) THF, HMPA, RT, 30 min 2: KF*2H2O / dimethylformamide / 0.5 h / Ambient temperature 3: 1) n-butyllithium / 1) THF, -23 deg C, 1 h, 2) THF, HMPA, 2.1) -23 deg C, 30 min., 2.2) RT, 1.5 h 4: 93 percent / 37percent HCl / methanol / Ambient temperature 5: 85 percent / pyridinium dichromate / dimethylformamide / Ambient temperature View Scheme

1.1: NH3; Li / dimethylsulfoxide / -78 - 25 °C 1.2: 98 percent / dimethylsulfoxide / 1 h / -78 - 25 °C 2.1: n-BuLi / tetrahydrofuran / 0.08 h / 0 °C 2.2: 61 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / 0 - 20 °C 3.1: 80 percent / NH3; Na / tetrahydrofuran / -78 - -33 °C 4.1: HCl / methanol / 16 h / 25 °C View Scheme