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With sodium periodate; In tetrahydrofuran; water; at 50℃; for 20h;Inert atmosphere;
The synthesis of 2 was previously published but, in this study, another synthetic route was employed. 1 (1.00 g, 3.40 mmol, 1.0 equiv.) was dissolved in 100 mL THF under N2 atmosphere. Dropwise, a solution of NaIO4 (7.27 g, 33.97 mmol, 10.0 equiv.) in H2O (100 mL) was added. The mixture was heated to 50 C for 20 h. During this time, the formation of a white suspension was observed. After this time, the solution was cooled down to room temperature and the solvent removed. The residue was dissolved in DCM and washed with H2O. The organic phase was dried over MgSO4, filtered and the solvent was removed by rotary evaporation. The product was dissolved in DCM and isolated by precipitation from pentane. The solid was obtained by filtration as apale yellow solid. Yield: 78%. Experimental data fits with the literature.
With selenium(IV) oxide; In 1,4-dioxane; for 44h;Inert atmosphere; Reflux;
General procedure: To a 100ml two-necked RB, dimethyl bipyridine 1 (500 mg, 0.00271 mol, 1.0 equiv.)was taken, added 100 mL of 1,4-dioxane drop wise and stirred to get a homogenous mixtureand the solution was purged with nitrogen for 15 min bubbling nitrogen into the dioxane withstirring. 0. 663 mg of SeO2 (2.2 equiv) was added and refluxed under N2 atmosphere for 44hours. After the completion of the reaction (Monitored by TLC), the reaction mixture waswashed with warm 1,4-dioxane for 2 to 3 minutes and filtered and 1, 4-dioxane was removedunder reduced pressure. The residue was then dissolved in hot distilled ethyl acetate, filteredand again washed with hot ethyl acetate. The ethyl acetate layer was washed with 1MNa2CO3 (250ml) to remove additional carboxylic acid. The organic layer was dried withanhydrous Na2SO4 and concentrated and the residue was purified on alumina using 60% ethylacetate in petroleum ether to afford the newly synthesized 2,2'-bipyridine 4,4'-dicarbaldehyde was thoroughly characterized by spectroscopic technique such as IR, 1HNMR, 13C NMR and HRMS.
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