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

Participants

Reaction Conditions

Reaction Steps

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.

Provenance & Evidence