Hydrochloric Acid → Ethyl 3-(furan-3-yl)-3-oxopropanoate

Temperature

60 °C

To a solution of 3-furancarboxylic acid (25.5 g, 227 mmol) in tetrahydrofuran (200 ml) was added 1,1′-carbonylbis-1H-imidazole (40.5 g, 250 mmol) and the mixture was stirred at 60° C. for 2 hrs. To the reaction solution was added monoethyl malonate magnesium salt (35.8 g, 125 mmol) and the mixture was heated under reflux for 30 min. Ethyl acetate (50 ml) and water (50 ml) were added the reaction solution, and conc. hydrochloric acid was added until the aqueous layer showed acidic pH. The reaction solution was extracted with ethyl acetate (200 ml×2). The extract was washed with saturated brine, dried over anhydrous magnesium sulfate and evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1) to give ethyl 3-(3-furanyl)-3-oxopropionate (42 g, 100%) as a colorless oil.

1. temperaturethe mixture was heated
2. temperatureunder reflux for 30 min
3. additionwas added until the aqueous layer
4. extractionThe reaction solution was extracted with ethyl acetate (200 ml×2)
5. washThe extract was washed with saturated brine
6. dry with materialdried over anhydrous magnesium sulfate
7. customevaporated under reduced pressure
8. customThe residue was purified by silica gel column chromatography (hexane:ethyl acetate=4:1)

ORD record

ord-ae7508bbde1c49619fc6dc1fb8c4b81d

Source dataset

uspto-grants-2006_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06982348B2