1: 1.) sodium hydride / 1.) dioxane, a) 10 min, b) RT, 1 h, c) reflux, 2 d, 2.) dioxane, a) 4 h, b) RT, 2 d, c) reflux, 32 h 2: 84 percent / perchloric acid, acetic acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 60 h View Scheme

in tetrahydrofuran 1.) 0 deg C, 4 h, 2.) RT, 2 d;

1: Et3N / dimethylformamide / 15.75 h / 0 - 25 °C 2: LiAlH4 / tetrahydrofuran / 12 h / Heating View Scheme

1: 45 percent / 30 h / 120 °C 2: 80 percent / sodium hydride / dioxane / 1.) RT, 10 min, 2.) reflux, 48 h 3: 84 percent / perchloric acid, acetic acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 60 h 4: 96 percent / thionyl chloride / heptane / 1.) RT, 10 min, 2.) reflux, 1 d 5: 83 percent / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) RT, 2 d View Scheme

1: 84 percent / perchloric acid, acetic acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 60 h 2: 96 percent / thionyl chloride / heptane / 1.) RT, 10 min, 2.) reflux, 1 d 3: 83 percent / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) RT, 2 d View Scheme

1: 80 percent / sodium hydride / dioxane / 1.) RT, 10 min, 2.) reflux, 48 h 2: 84 percent / perchloric acid, acetic acid / 1.) 0 deg C, 10 min, 2.) RT, 30 min, 3.) reflux, 60 h 3: 96 percent / thionyl chloride / heptane / 1.) RT, 10 min, 2.) reflux, 1 d 4: 83 percent / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) RT, 2 d View Scheme

1: 96 percent / thionyl chloride / heptane / 1.) RT, 10 min, 2.) reflux, 1 d 2: 83 percent / tetrahydrofuran / 1.) 0 deg C, 4 h, 2.) RT, 2 d View Scheme

lithium aluminium tetrahydride in tetrahydrofuran 12 h; Heating;