Pyridine → Ethyl 5-(4-methylphenyl)-1,3,4-oxadiazole-2-carboxylate

Participants

Reaction Steps

6A (8.1 g, 32.4 mmol) was dissolved in toluene (200 ml) and pyridine (2.6 mL, 32.4 mmol). Thionyl chloride (9.6 g, 81 mmol) was added and the reaction was refluxed for 8 h. The solvent was evaporated and the residue was partitioned between DCM and aqueous NaHCO3 (sat.). The organic phase was further washed with 0.1 M HCl and aqueous NaHCO3 (sat.), filtered through a phase separator and the solvent was removed by evaporation. There was obtained 7.0 g (93%) of 6B as an off white solid. 1H NMR (400 MHz, CDCl3): δ 1.48 (t, 3H), 2.44 (s, 3H), 4.54 (q, 2H), 7.34 (d, 2H), 8.04 (d, 2H).

Provenance & Evidence