Hydrochloric Acid → HCID 9990260, compound

Sodium hydride (60% in oil, 629 mg) was added to a solution of tert-butyl 3-(2-furyl)-3-oxopropionate (3.01 g) in tetrahydrofuran (80 ml) at 0° C. and stirred for 10 minutes. Ethyl bromoacetate (1.51 ml) was added to the mixture, and then the resultant was stirred at room temperature for 4 hours, 0.1N hydrochloric acid (200 ml) was added and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgS04) and concentrated. The residue was subjected to silica gel chromatography to obtain an oil from and ethyl acetate-hexane (1:5, v/v)-eluted fraction. This was dissolved in toluene (150 ml), and trifluoroacetic acid (2.64 ml) was added, and then the reaction mixture was stirred at 90° C. for 6 hours. An aqueous saturated solution of sodium bicarbonate was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residue was subjected to silica gel chromatography to obtain ethyl 4-(2-furyl)-4-oxobutyrate (2.22 g, yield 79%) as a colorless oil from an ethyl acetate-hexane (1:3, v/v)-eluted fraction.

1. stirringthe resultant was stirred at room temperature for 4 hours
2. extractionextracted with ethyl acetate
3. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
4. customdried (MgS04)
5. concentrationconcentrated
6. customto obtain an oil from and ethyl acetate-hexane (1:5, v/v)-eluted fraction
7. stirringthe reaction mixture was stirred at 90° C. for 6 hours
8. extractionextracted with ethyl acetate
9. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
10. dry with materialdried (MgSO4)
11. concentrationconcentrated

ORD record

ord-0da1595adb6d485688e52b6a35d5b9b8

Source dataset

uspto-grants-2002_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06495581B1