Hydrochloric Acid → Benzenepropanoic acid, 4-nitro-beta-oxo-, ethyl ester

Under nitrogen atmosphere, 30 mL of THF was added to 6.09 g (10 mmol, 1.0 equivalent) of (BrZnCH2COOEt.THF)2. Under argon atmosphere, a solution of 1.48 g (10 mmol) of p-nitrobenzonitrile in 10 mL of THF was added dropwise while stirring at 0˜5° C. The mixture was stirred at 20˜25° C. for 21 hours. 15 mL of 10% hydrochloric acid was added dropwise at 20° C. or lower, and the mixture was stirred at 20˜25° C. for 2 hours, followed by dilution with 50 mL of ethyl acetate. Then, the layers were separated. The organic layer was washed successively with 15 mL of 1N hydrochloric acid, 20 mL of an aqueous saturated sodium chloride solution, 20 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 20 mL of an aqueous saturated sodium chloride solution. After washing, the organic layer was dried with anhydrous magnesium sulfate. After concentration under reduced pressure, crystals were loosened with n-hexane, filtered, and washed with n-hexane. After vacuum drying (40° C.), 2.09 g of the desired product was obtained (yield 88%).

1. stirringThe mixture was stirred at 20˜25° C. for 21 hours
2. stirringlower, and the mixture was stirred at 20˜25° C. for 2 hours
3. customThen, the layers were separated
4. washThe organic layer was washed successively with 15 mL of 1N hydrochloric acid, 20 mL of an aqueous saturated sodium chloride solution, 20 mL (×2) of an aqueous saturated sodium bicarbonate solution, and 20 mL of an aqueous saturated sodium chloride solution
5. washAfter washing
6. dry with materialthe organic layer was dried with anhydrous magnesium sulfate
7. concentrationAfter concentration under reduced pressure, crystals
8. filtrationfiltered
9. washwashed with n-hexane
10. customAfter vacuum drying (40° C.)

ORD-Eintrag

ord-b9ca9ca5c5174c28b0da0db993d714c1

Quelldatensatz

uspto-grants-2010_02

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US07662974B2