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

Temperature

50 °C

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.

1. temperatureAfter cooling to room temperature
2. concentrationthe mixture was concentrated under reduced pressure, and water (30 ml)
3. additionwas added to the residue
4. extractionThe mixture was extracted 3 times with ethyl acetate
5. washthe combined organic layer was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. concentrationconcentrated to about 50 ml under reduced pressure, and hexane (200 ml)
8. additionwas added
9. concentrationThe mixture was concentrated again to about 50 ml under reduced pressure
10. filtrationthe precipitate was collected by filtration
11. washwashed 3 times with hexane
12. customdried under reduced pressure

ORD record

ord-916f7e2251af4f8f8d58159058e24d1a

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2