Acetic Acid → methyl (2E)-3-(4-formylthiophen-2-yl)acrylate

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl (2E)-3-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]acrylate (3.050 g, 12.69 mmol) in tetrahydrofuran (10 ml) were added acetic acid (30 ml) and water (10 ml), and the mixture was stirred at 50° C. for 2 hr. After cooling to room temperature, the mixture was concentrated under reduced pressure, and water (30 ml) was added to the residue. The mixture was extracted 3 times with ethyl acetate, and the combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, concentrated to about 50 ml under reduced pressure, and hexane (200 ml) was added. The mixture was concentrated again to about 50 ml under reduced pressure, and the precipitate was collected by filtration, washed 3 times with hexane, and dried under reduced pressure to give methyl (2E)-3-(4-formylthiophen-2-yl)acrylate (2.213 g, 11.28 mmol, 88.9%) as a white solid.

Provenance & Evidence