Hydrogenation;

water; sodium acetate in ethanol 5 h; Reflux;

1: 93 percent / benzene / 48 h / Heating 2: 86 percent / 90percent trifluoroacetic acid / 0.17 h / Ambient temperature 3: 32 percent / potassium acetate / 0.17 h / Heating View Scheme

1: 88 percent / NaBH3CN, H2O, AcOH, HCl / tetrahydrofuran / 1 h / Ambient temperature 2: 98 percent / acetonitrile / 2 h / Heating 3: DCC, DMAP / CH2Cl2 / Ambient temperature 4: Et3N / dioxane / Heating 5: 90 percent / KOH / ethanol / 1 h / Heating 6: 93 percent / imidazole / dimethylformamide / 24 h / Ambient temperature 8: Ph2PLi / tetrahydrofuran; hexane / 16 h / Heating 9: Bu4NF / tetrahydrofuran / Ambient temperature View Scheme

boron trifluoride diethyl etherate in 1,4-dioxane T=50°C;