1: 95 percent / AcCl / 48 h / 20 °C 2: 98 percent / K2CO3 / ethanol / 20 h / Heating View Scheme

1: 96 percent / cc. H2SO4 / 8 h / Heating 2: 1.) sodium hydride (NaH) / 1.) tetrahydrofuran (THF), 0 deg C to room temp., 1 h; 2.) THF, 0 deg C to room temp., 8 h View Scheme

thionyl chloride in nitrobenzene 2 h; Heating / reflux;

N,N,N',N',N'',N''-hexamethylphosphoric triamide; sodium hydroxide T=20°C; 52 h;

1: SOCl2 / dioxane / 3 h / 100 °C 2: dioxane / 6 h / 100 °C View Scheme

pyridin-4-yl methyl amine; dicyclohexyl-carbodiimide in dichloromethane; N,N-dimethyl-formamide 2 h; Ambient temperature;

pyridin-4-yl methyl amine; 2-phenyl-ethanol in dichloromethane; N,N-dimethyl-formamide 2 h; Ambient temperature;

1: 1-carboxy-2-(3,4-dihydroxyphenyl)ethylene With thionyl chloride in 1,4-dioxane 1 h; Heating; 2: butan-1-ol in 1,4-dioxane Heating; Further stages.;

1: SOCl2 / dioxane / 3 h / 100 °C 2: dioxane / 6 h / 100 °C View Scheme

1: 96 percent / cc. H2SO4 / 8 h / Heating 2: 1.) sodium hydride (NaH) / 1.) tetrahydrofuran (THF), 0 deg C to room temp., 1 h; 2.) THF, 0 deg C to room temp., 8 h 3: 78 percent / lithium aluminum hydride / diethyl ether; tetrahydrofuran / -10 °C 4: 84 percent / tert-butyl hydroperoxide (70percent), vanadyl acetylacetonate / H2O; CH2Cl2 / 6 h / Ambient temperature 5: 81 percent / aq. sodium hydroxide (1percent) / 2.5 h / 70 °C 6: 72 percent / CH2Cl2; pyridine / 6 h / -10 °C 7: 99 percent / potassium carbonate (K2CO3) / methanol / 0.5 h / Ambient temperature 8: 95 percent / H2 / Pd-C (5percent) / ethyl acetate 9: 86 percent / potassium carbonate (K2CO3) / methanol / 0.5 h / Ambient temperature 10: 1.) sodium hydride (NaH) / 1.) THF, 0 deg C, 1 h; 2.) THF, room temp., 1 h 11: 76 percent / HCl (2N) / methanol / 2 h / Ambient temperature View Scheme