1: 81 percent / KOH, PEG-200 / 2 h / Heating 2: 97 percent / Ph3P*Br2, pyridine / CCl4; CH2Cl2 / Ambient temperature 3: 1.) NaNH2, DMPU / 1.) THF, 2 h, 2.) THF, -from -10 deg C to RT, 10 h 4: 1.) NaNH2, DMPU / 1.) THF, 2 h, 2.) THF, -from -10 deg C to RT, overnight 5: aq. PTSA / methanol / 0.75 h / Heating 6: 99 percent / LiAlH4 / tetrahydrofuran / Ambient temperature 7: 98 percent / H2, quinoline / Pd/BaSO4 / hexane / 4 h / Ambient temperature View Scheme

1: 60 percent / NaNH2 / liquid ammonia 2: 1) 1,3,2-benzodioxaborole, then hydrolysis; 2) NaOH/I2 View Scheme

sodium methylate Yield given;