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ChemicalBook CAS DataBase List Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate
571-55-1

Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate synthesis

3synthesis methods
Triethyl orthoformate

122-51-0

Ethyl 4,4,4-trifluoroacetoacetate

372-31-6

Ethyl 2-(ethoxymethylene)-4,4,4-trifluoroacetoacetate

571-55-1

General procedure for the synthesis of ethyl ethoxy-2-methylene trifluoroacetoacetate from triethyl orthoformate and ethyl trifluoroacetoacetate: ethyl 4,4,4-trifluoro-3-oxobutanoate (30 g, 162.9 mmol) was added to a solution of acetic anhydride (50 mL) containing triethoxymethane (72.4 g, 488.8 mmol). The reaction mixture was stirred continuously at 135 °C for 18 hours. Upon completion of the reaction, the brown mixture was concentrated to afford ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate (38 g, 97.1% yield), the product was a brown oil that could be used in subsequent reactions without further purification. The product was characterized by 1H NMR (400 MHz, CDCl3): δ 1.23-1.33 (m, 3H), 1.40 (dt, J = 14.18, 7.19 Hz, 3H), 4.19-4.36 (m, 4H), 7.66-7.87 (m, 1H).

-

Yield:571-55-1 97.1%

Reaction Conditions:

with acetic anhydride at 135; for 18 h;

Steps:

1.E E.
Ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate, 1f

Ethyl 4,4,4-trifluoro-3-oxobutanoate (30 g, 162.9 mmol) was added to a solution of triethoxymethane (72.4 g, 488.8 mmol) in acetic anhydride (50 mL).
The mixture was stirred at 135° C. for 18 h.
The brown mixture was concentrated to afford ethyl 2-(ethoxymethylene)-4,4,4-trifluoro-3-oxobutanoate, 1f (38 g, 97.1%) as a brown oil, which was used in the following reaction without further purification. 1H NMR (400 MHz, CDCl3) δ ppm 1.23-1.33 (m, 3H) 1.40 (dt, J=14.18, 7.19 Hz, 3H) 4.19-4.36 (m, 4H) 7.66-7.87 (m, 1H).

References:

US2018/170909,2018,A1 Location in patent:Paragraph 0824; 0825

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