2-(2'-Cinnamyl-1',3'-oxazolyl)-1,3-dithiolane

Abstract

To a mixture of 2-cinnamyl-1,3-oxazole-4-carboxaldehyde [1,2] (2.8 g, 14 mmol) and ethanedithiol (2.3 g, 21 mmol) in methylene chloride (100 ml) was added boron trifluoride etherate (2.8 g, 21 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was washed with aqueous sodium hydroxide (5%, 50 ml), and aqueous phase was extracted with ether. The combined organic layers were dried (MgSO 4 ), and concentrated. The residue was purified by column chromatography (SiO 2 , 3:1 hexanes/ethyl acetate) to give 2-(2'-cinnamyl-1',3'-oxazolyl)-1,3-dithiolane as a light yellow solid (2.25 g, 66%).