tert.-butylhydroperoxide; acetic anhydride; p-benozquinone; palladium diacetate in acetic acid T=50°C; 12 h;

chromium dichloride in tetrahydrofuran T=20°C; 12 h;

molecular sieve; diphenyl phosphoryl azide; triethylamine in tert-butyl alcohol 36 h; Heating;

1: 68 percent / aq. ethanol / 3 h / Heating 2: 90 percent / 15 percent NaOH / 8 h / Heating 3: 95 percent / 4-(Dimethylamino)pyridine, pyridine, SOCl2 / 12 h / 1.) -50 deg C to r. t.; 2.) 12 h, room temp. 4: 0.1 N NaOH / dioxane; H2O; methanol / 27 h 5: 80 percent / triethylamine, diphenyl-azidophosphate, molecular sieve / 2-methyl-propan-2-ol / 36 h / Heating View Scheme

1: 95 percent / 4-(Dimethylamino)pyridine, pyridine, SOCl2 / 12 h / 1.) -50 deg C to r. t.; 2.) 12 h, room temp. 2: 0.1 N NaOH / dioxane; H2O; methanol / 27 h 3: 80 percent / triethylamine, diphenyl-azidophosphate, molecular sieve / 2-methyl-propan-2-ol / 36 h / Heating View Scheme

1: 0.1 N NaOH / dioxane; H2O; methanol / 27 h 2: 80 percent / triethylamine, diphenyl-azidophosphate, molecular sieve / 2-methyl-propan-2-ol / 36 h / Heating View Scheme

in toluene Wittig reaction;

sodium hydride; malonic acid dimethyl ester 1.) 50 deg C, 16 h, 2.) dimethoxyethane, RT, 25 h; Yield given. Multistep reaction. Yields of byproduct given;

sodium hydride Yield given. Multistep reaction. Yields of byproduct given;