hydrogenchloride in 1,4-dioxane 4.5 h; Heating;

argentic oxide; nitric acid in 1,4-dioxane 0.166667 h; Ambient temperature;

1: 93 percent / K2CO3 / acetone / 5 h / Ambient temperature 2: 1.) MeLi / 1.) Et2O, 0 deg C, 20 min, 2.) Et2O, 0 deg C, 60 min 3: 1.) n-BuLi / 1.) hexane, Et2O, a) 0 deg C, 10 min, b) RT, 24 h, 2.) hexane, Et2O, 30 min 4: 80 percent / triethylsilane, BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 5: 56 percent / silver(II) oxide, 7 N aq. nitric acid / dioxane / 0.17 h / Ambient temperature View Scheme

1: 93 percent / m-chloroperoxybenzoic acid / CHCl3 / 1.5 h / Heating 2: 93 percent / K2CO3 / acetone / 5 h / Ambient temperature 3: 1.) MeLi / 1.) Et2O, 0 deg C, 20 min, 2.) Et2O, 0 deg C, 60 min 4: 1.) n-BuLi / 1.) hexane, Et2O, a) 0 deg C, 10 min, b) RT, 24 h, 2.) hexane, Et2O, 30 min 5: 80 percent / triethylsilane, BF3*Et2O / CH2Cl2 / 0.5 h / -78 °C 6: 56 percent / silver(II) oxide, 7 N aq. nitric acid / dioxane / 0.17 h / Ambient temperature View Scheme