Reaktion #507423

Reaktionsgleichung

ethyl acetate

BrZnCH2COOEt

anisonitrile

hydrochloric acid

→

desired product

Ausbeute 94.0%

ethyl 3-(4-methoxyphenyl)-3-oxopropanoate

Ausbeute 94.0%

Lösungsmittel

THF

THF

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.STIRRINGThe mixture was stirred at 20˜25° C. for 92 hours
2. 2
   workup.STIRRINGlower, and the mixture was stirred at 20˜25° C. for 1 hour and 35 minutes
3. 3
   SonstigeThen, the layers were separated
4. 4
   WaschenThe 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. 5
   WaschenAfter washing
6. 6
   Trocknenthe organic layer was dried with anhydrous magnesium sulfate
7. 7
   EinengenConcentration under reduced pressure

Vorschrift

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 1.33 g (10 mmol) of anisonitrile in 5 mL of THF was added dropwise while stirring at 0˜5° C. The mixture was stirred at 20˜25° C. for 92 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 1 hour and 35 minutes, 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. Concentration under reduced pressure afforded 2.08 g of the desired product (yield 94%).

Quelle