lithium aluminium tetrahydride in tetrahydrofuran 10 h; Heating;

1: 1.) NaH / 1.) THF, RT, 30 min, 2.) THF, RT, 3 h 2: 94 percent / LiAlH4 / tetrahydrofuran / 10 h / Heating View Scheme

Multistep reaction;

1: 1.) sodium hydride / 1.) DMF, 70 deg C, 4 h, 2.) 70 deg C, 6 days 2: 99 percent / conc. HCl / CH2Cl2; methanol / 2 h / Ambient temperature 3: 70 percent / NaOH, p-toluenesulfonyl chloride / dioxane / 24 h / 60 °C View Scheme

potassium tert-butylate in tetrahydrofuran 72 h; Heating;

1: 50percent aq. sodium hydroxide / tetrabutylammonium hydrogen sulfate / 72 h / 65 °C 2: aq. HCl / methanol; CH2Cl2 / 2 h / Ambient temperature View Scheme