ChemicalBook CAS DataBase List Ethyl 2-phenylacetoacetate

Ethyl 2-phenylacetoacetate synthesis

9synthesis methods

Product Name:Ethyl 2-phenylacetoacetate
CAS Number:5413-05-8
Molecular formula:C12H14O3
Molecular Weight:206.24

A flame-dried flask was charged with 10 mmol (1 equiv) of sublimed potassium tert-butoxide in anhydrous DMF (50 mL) at room temperature under argon. Then, 10 mmol (1 equiv) of freshly distilled EAA was added to the reaction mixture and stirred for 30 min at 0 °C, followed by dropwise addition of diaryliodonium salt (4 mmol, 0.4 equiv to EAA) in 10 mL of DMF. Reaction was left stirring at room temperature for the time mentioned in the table. After confirming complete consumption of iodonium salt (by LCMS), to the reaction mixture was added 1 M HCl in one portion to bring the pH to around 5.0. The crude was extracted with diethyl ether until the aqueous layer was devoid of product. The organic layer was dried over sodium sulfate, and solvent was removed in vacuo. The product was purified by flash column chromatography (0.5-2% of hexane in ethyl acetate). Ethyl 2-phenylacetoacetate 1H NMR (500 MHz, CDCl3) δ 13.13 (s, 0.3H), 7.41-7.27 (m, 4H), 7.18-7.13 (m, 1H), 4.69 (s, 0.7H), 4.27-4.15 (m, 2H), 2.19 (s, 2H), 1.86 (s, 1H), 1.28 (t, J = 7.1 Hz, 2H), 1.18 (t, J = 7.1 Hz, 1H). 13C NMR (126 MHz, CDCl3) δ 201.7, 174.0, 172.7, 168.6, 135.4, 132.8, 131.4, 129.4, 129.0, 128.4, 128.1, 127.0, 104.5, 65.9, 61.8, 60.8, 28.9, 20.0, 14.3, 14.2. HRMS (ESI-TOF) m/z: [M + H]+ calcd for C12H14O3 207.1016; found 207.1018.
synthesis of Ethyl 2-phenylacetoacetate.jpg

synthesis of Ethyl 2-phenylacetoacetate.jpg

108-24-7
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101-97-3 Synthesis

101-97-3
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5413-05-8
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$165.00/1g

Yield:5413-05-8 61%

Reaction Conditions:

Stage #1: Ethyl 2-phenylethanoatewith sodium hydride in tetrahydrofuran at 60; for 0.5 h;Cooling with ice;
Stage #2: acetic anhydride in tetrahydrofuran at 0 - 20; for 1 h;

Steps:

1.B B Ethyl 2-phenylacetoacetate (Intermediate 2)

NaH (326 mg, 8.15 mmol) was suspended in 15 mL of dry THF.Ethyl phenylacetate (1 mL, 6.27 mmol) was added dropwise under ice bath.After the completion of the dropwise addition, the reaction was carried out at 60 ° C for 30 min.The reaction solution was cooled to 0 ° C.Add 2 mL of acetic anhydride (655 μL, 7 mmol) in THF.After the completion of the dropwise addition, the mixture was transferred to room temperature, and the reaction was continued for 1 hour.After the reaction was completed, the reaction solution was poured into ice water and extracted with EtOAc.The organic phase is washed with water, saturated with NaHCO3, and washed with saturated NaCl.Dry with anhydrous Na2SO4. concentrate,Separated by column chromatography (petroleum ether: EtOAc = 10:1).A yellow oily liquid 789 mg was obtained. Υield 61%:

References:

CN108997242,2018,A Location in patent:Paragraph 0034; 0037; 0038

591-50-4 Synthesis