mercury(II) trifluoroacetate; sodium hydrogencarbonate 1.) CH2Cl2, 24 h, 2.) CH2Cl2; Yield givenMultistep reaction. Further byproducts given. Yields of byproduct given;

1: NaBH4; THF 2: toluene-4-sulfonic acid View Scheme

1: 2,6-dimethylpyridine / dichloromethane / 2 h / 20 °C 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 65 - 67 °C / |Reflux 3: sodium hydroxide / water; methanol / 70 - 75 °C 4: triethylamine; 4-(N,N-dimethlyamino)pyridine / tetrahydrofuran / 24 h / 20 - 25 °C View Scheme

1: 2,6-dimethylpyridine / dichloromethane / 2 h / 20 °C 2: sodium carbonate; bis-triphenylphosphine-palladium(II) chloride / tetrahydrofuran; water / 65 - 67 °C / |Reflux 3: sodium hydroxide / water; methanol / 70 - 75 °C View Scheme