1: 87 percent / tetrabutylammonuim hydrogen sulfate; sodium hidroxide / CH2Cl2 / 20 °C 2: TiCl4; zinc powder / tetrahydrofuran / Heating 3: 100 percent / MeONa / dimethylformamide / 1.5 h 4: 73 percent / K2CO3 / acetone; H2O / 4 h / Heating 5: 100 percent / hydrogen / 10percent palladium on carbon / ethyl acetate / 2.5 h / 760.05 Torr View Scheme

1: Zn, TiCl4 / tetrahydrofuran 2: H2 / Pd/C / 2 h / Ambient temperature View Scheme