2,3-dicyano-5,6-dichloro-p-benzoquinone in benzene 2 h; Inert atmosphereReflux;

1: 4-methoxy-6-vinyl-2H-pyran-2-one With sodium acetate; palladium diacetate in acetonitrile Heck-Matsuda reaction; 0.166667 h; 2: 4-methoxybenzenediazonium tetrafluoroborate in acetonitrile Heck-Matsuda reaction;

sodium ethanolate in ethanol; N,N-dimethyl-formamide 16 h; Ambient temperature;

1: potassium carbonate / acetone / Inert atmosphere; Reflux 2: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 3: n-butyllithium; triphenyl-methyl-phosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 4: sodium acetate; palladium diacetate / acetonitrile / 0.17 h View Scheme

1: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 2: n-butyllithium; triphenyl-methyl-phosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 3: sodium acetate; palladium diacetate / acetonitrile / 0.17 h View Scheme

1: [Pd2(dibenzylideneacetone)3]*dibenzylideneacetone; sodium acetate / 1 h / 80 °C / Microwave irradiation 2: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Inert atmosphere; Reflux View Scheme

1: sulfuric acid / 0.25 h / 130 °C / Cooling with ice 2: potassium carbonate / acetone / Inert atmosphere; Reflux 3: selenium(IV) oxide / 1,4-dioxane / 5 h / 180 °C / Inert atmosphere; Sealed tube 4: n-butyllithium; triphenyl-methyl-phosphonium iodide / tetrahydrofuran / 3 h / -78 - 20 °C / Inert atmosphere 5: sodium acetate; palladium diacetate / acetonitrile / 0.17 h View Scheme

1: potassium carbonate / acetone / 20 h / 20 °C / Inert atmosphere 2: [Pd2(dibenzylideneacetone)3]*dibenzylideneacetone; sodium acetate / 1 h / 80 °C / Microwave irradiation 3: 2,3-dicyano-5,6-dichloro-p-benzoquinone / toluene / 2 h / Inert atmosphere; Reflux View Scheme

1: 1.) COCl2, 2.) triethylamine / 1.) RT, 18 h, 2.) petroleum ether, CH2Cl2, 0 deg C, 30 min 2: 53 percent / 60 percent NaH, 1.46 M n-BuLi / tetrahydrofuran; hexane / 20 min, rt; 0 deg C, 10 min; 0 deg C, 1-2 h 3: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 4: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme

1: 53 percent / 60 percent NaH, 1.46 M n-BuLi / tetrahydrofuran; hexane / 20 min, rt; 0 deg C, 10 min; 0 deg C, 1-2 h 2: 1.) TFA, 2.) acetic anhydride / 1.) CH2Cl2, rt, 1 h, 2.) rt, 18 h 3: K2CO3 / dimethylformamide / 18 h / Ambient temperature View Scheme