1: 1.) NaH / 1.) DMF, hexane, RT, 1 h, 2.) DMF, hexane, RT, 2 h 2: 82 percent / CuSO4*5H2O / methanol; H2O / 10 h 3: 80 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene / benzene / 30 h / Heating View Scheme

1: 98 percent / CH3ONa / tetrahydrofuran / 20 h / Ambient temperature 2: 97 percent / glacial CH3COOH, H2O / tetrahydrofuran / 18 h / 70 °C 3: 90 percent / H2 / Raney Ni / methanol / 8 h / 100 °C View Scheme

1: NaH / dimethylformamide / 1 h / 27 - 30 °C 2: CuSO4*5H2O / methanol; H2O / 1.5 h / 60 °C View Scheme