1: 73 percent / Na2CO3 / Pd(0)/C / 1,2-dimethoxy-ethane; H2O / 1 h / 45 °C 2: 85 percent / pTsOH / methanol; tetrahydrofuran / 1 h / 60 °C View Scheme

1: tetrakis(triphenylphosphine) palladium(0); sodium carbonate / water; ethanol; toluene / 1 h / 130 °C / |Inert atmosphere; |Microwave irradiation 2: toluene-4-sulfonic acid; hydrogenchloride / tetrahydrofuran; methanol / 1 h / 60 °C View Scheme

1: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 2: 3-Methylpyridine / anhydrous xylene / 24 h / |Reflux 3: sodium carbonate; palladium on activated charcoal / ethylene glycol dimethyl ether; water / 1 h / 45 °C 4: toluene-4-sulfonic acid / methanol; tetrahydrofuran / 1 h / 60 °C 5: potassium carbonate / acetone / 20 °C View Scheme