tetrabutyl ammonium fluoride in tetrahydrofuran 2.5 h; Ambient temperature;

1: diisobutylaluminium hydride / toluene / 2 h / -78 °C 2: 1.) NaH / 1.) benzene, RT, 30 min, 2.) toluene, benzene, RT, overnight 3: 81.2 percent / H2 / 5 percent Pd-C / methanol / 5 h / Ambient temperature 4: 97 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 5: 90 percent / n-Bu4NF / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

1: 1.) NaH / 1.) benzene, RT, 30 min, 2.) toluene, benzene, RT, overnight 2: 81.2 percent / H2 / 5 percent Pd-C / methanol / 5 h / Ambient temperature 3: 97 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 4: 90 percent / n-Bu4NF / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

1: 81.2 percent / H2 / 5 percent Pd-C / methanol / 5 h / Ambient temperature 2: 97 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 3: 90 percent / n-Bu4NF / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

diethyl ether; magnesium T=-75°C;

1: 97 percent / pyridine / CH2Cl2 / 12 h / Ambient temperature 2: 90 percent / n-Bu4NF / tetrahydrofuran / 2.5 h / Ambient temperature View Scheme

potassium hydroxide in methanol 0.5 h; Ambient temperature;