2-Acetylfuran → 4,4,4-Trifluoro-1-(2-furanyl)-1,3-butanedione

The diketone 19 was synthesized from acetylfuran and trifluoracetate to obtain the 4,4,4-trifluoro-1-(furan-2-yl)butane-1,3-dione 19 product as follows. 2-Acetylfuran 18 (11.0 g, 210 mmol) was dissolved in benzene (210 mL). At room temperature was added KOtBu (23.6 g, 210 mol). The resulting red solution was cooled to 5° C. Ethyl trifluoracetate 6 (25 mL, 29.8 g, 210 mmol) was added dropwise in approximately 20 minutes keeping the temperature below 15° C. Then the mixture was stirred for 16 hours at room temperature. The mixture was poured in ice-water (300 mL) containing concentrated sulfuric acid (5 g). The aqueous mixture was extracted with tBME (3×200 mL). The combined organic layers were washed with brine (200 mL), dried (Na2SO4) and concentrated to give a dark brown oil (20.8 g). The crude product was purified by kugelrohr distillation to give compound 19 (17.0 g, 39%) as a yellowish oil.

ORD record

ord-b3d89faae4f2460e8446120a6d733fa4

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809344B2