Water → methyl (2E)-3-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]acrylate

Temperature

0 °C

To a solution of methyl (2E)-3-[4-(1,3-dioxolan-2-yl)-5-(trimethylsilyl)thiophen-2-yl]acrylate (4.000 g, 12.80 mmol) in tetrahydrofuran (20 ml) was added water (0.2 ml), and the mixture was cooled to 0° C. Tetrabutylammoniumfluoride tetrahydrofuran solution (1M, 13.4 ml, 13.4 mmol) was added, and the mixture was stirred at 0° C. for 5 min and at room temperature for 10 min. The mixture was cooled to 0° C., saturated aqueous ammonium chloride solution (40 ml) was added, and the mixture was extracted 3 times with ethyl acetate. The combined organic layer was washed with saturated brine, dried over anhydrous magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:hexane=1:3) to give methyl (2E)-3-[4-(1,3-dioxolan-2-yl)thiophen-2-yl]acrylate (3.065 g, 12.76 mmol, 99.7%) as a colorless oil.

1. temperatureThe mixture was cooled to 0° C.
2. extractionthe mixture was extracted 3 times with ethyl acetate
3. washThe combined organic layer was washed with saturated brine
4. dry with materialdried over anhydrous magnesium sulfate
5. concentrationconcentrated under reduced pressure
6. customThe residue was purified by silica gel column chromatography (FUJI SILYSIA CHEMICAL LTD. BW-300SP 200 g, ethyl acetate:hexane=1:3)

ORD record

ord-ec7933736cd548c1b1a10e798e38bac7

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08507690B2