pyridine in dichloromethane T=20°C;

1: 75 percent / pyridine / CH2Cl2 / 20 °C 2: 74 percent / sodium bicarbonate; m-chloroperoxybenzoic acid / CH2Cl2 / 41 h 3: 69 percent / H2 / Pd/C / ethyl acetate / 23 h View Scheme

1.1: 80 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2.1: mercuric acetate / H2O; tetrahydrofuran / 24 h / 20 °C 2.2: 15 percent / sodium hydroxide; sodium borohydride / H2O; tetrahydrofuran / 0.75 h View Scheme

1: 80 percent / pyridine / CH2Cl2 / 1 h / 20 °C 2: 75 percent / chlorine / CCl4; CH2Cl2 / 20 °C 3: 74 percent / potassium tert-butoxide / tetrahydrofuran / 24 h View Scheme