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Chemistry
Organic Building Blocks
Fluorinated Building Blocks
Diethyl 2-(2,2,2-trifluoroacetyl)succinate
Chemistry
Organic Building Blocks
Fluorinated Building Blocks
Esters Ketones Trifluoromethyls Aliphatic Chain Hydrocarbons

[ CAS No. 94633-25-7 ] {[proInfo.proName]}

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Chemical Structure| 94633-25-7
Chemical Structure| 94633-25-7
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Product Details of [ 94633-25-7 ]

CAS No. :94633-25-7 MDL No. :MFCD07779768
Formula : C10H13F3O5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 270.20 Pubchem ID :-
Synonyms :

Safety of [ 94633-25-7 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P501-P270-P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313-P301+P312+P330 UN#:N/A
Hazard Statements:H302-H315-H319 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 94633-25-7 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

  • Downstream synthetic route of [ 94633-25-7 ]

[ 94633-25-7 ] Synthesis Path-Downstream   1~2

  • 1
  • [ 94633-25-7 ]
  • [ 70961-05-6 ]
YieldReaction ConditionsOperation in experiment
62% With boric acid at 170℃; for 3h; Heating;
53% at 170℃; for 5h;
43% With boric acid at 170℃; for 4h; 37 In a one-necked round-bottomed flask equipped with a distillation head and cooler, a mixture of 2-(2,2,2-trifluoro-acetyl)-succinic acid diethyl ester (54.6 g, 202 mmol) and boronic acid (12.5 g, 202 mmol) is heated to 170 0C. Heating is continued for 4 h, during which time ethanol is gradually distilled off as it is formed. After cooling to room temperature, the reaction mixture is poured onto ice and extracted twice with EtOAc. The combined organic layers are washed with brine, dried over Na2SO4 and concentrated at reduced pressure to afford a brown oil. The crude product is purified by distillation (60 0C, 10 mbar) to afford the title compound as a colorless liquid (17.3 g, 87.3 mmol, 43 %). 1H NMR (400 MHz, CDCI3, 298 K): δ = 4.15 (q, J = 7.1 Hz, 2H), 3.02 (t, J = 6.4 Hz, 2H), 2.70 (t, J = 6.4 Hz, 2H), 1.45 (t, J = 7.1 Hz, 3H). MS (ES+): 199 (M(C7H9F3O3^H)+.
With sulfuric acid
With sulfuric acid for 4h; Heating;
With boric acid; toluene-4-sulfonic acid 28.B STEP B: STEP B: Ethyl 5,5,5-trifluoro-4-oxo-pentanoate 45 g of the product of Step A, 10.3 g of boric acid and 1 g of p-toluenesulfonic acid were heated at 180° C. for 3 hours and the mixture was poured into ice and extracted with ethyl acetate. The mixture was decanted, dried and concentrated under reduced pressure and the residue was distilled to obtain 10.8 g of expected product.
With boric acid at 150 - 180℃; for 3h; Inert atmosphere;

Reference： [1]Ratier, Max; Pereyre, Michel; Davies, Alwyn G.; Sutcliffe, Roger [Journal of the Chemical Society. Perkin transactions II, 1984, p. 1907 - 1916]
[2]De Meijere, Armin; Kozhushkov, Sergei I.; Yufit, Dmitrii S.; Grosse, Christian; Kaiser, Marcel; Raev, Vitaly A. [Beilstein Journal of Organic Chemistry, 2014, vol. 10, p. 2844 - 2857]
[3]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - WO2008/74752, 2008, A2 Location in patent: Page/Page column 32-33
[4]Hanack,M.; Meyer,H. [Justus Liebigs Annalen der Chemie, 1968, vol. 720, p. 81 - 97]
[5]Brown,P. et al. [Tetrahedron, 1960, vol. 10, p. 164 - 170]
[6]Current Patent Assignee: SANOFI - US5064861, 1991, A
[7]Location in patent: experimental part Wan, Wen; Hou, Jie; Jiang, Haizhen; Wang, Yangli; Zhu, Shizheng; Deng, Hongmei; Hao, Jian [Tetrahedron, 2009, vol. 65, # 21, p. 4212 - 4219]
  • 2
  • [ 383-63-1 ]
  • [ 123-25-1 ]
  • [ 94633-25-7 ]
YieldReaction ConditionsOperation in experiment
78% Under an argon atmosphere, trifluoroacetic acid ethyl ester (107 ml_, 899 mmol) is added dropwise during 30 min. to a 60 % suspension of NaH in mineral oil (22.6 g, 940 mmol). The resulting white suspension is heated to 60 0C and succinic acid ethyl ester (62.0 ml_, 370 mmol) is added dropwise during 5 h. The reaction mixture is heated for 18 h at 65 0C, cooled down to room temperature and carefully added to a mixture of ice (130 mg) and a 6 M aqueous H2SO4 solution (200 ml_). The dark brown solution is extracted twice with TBME and the combined organic phases are washed with brine, dried over Na2SO4 and concentrated at reduced pressure to afford a brown oil. The crude product is purified by bulb- to-bulb distillation (100-120 0C, 1 mbar) to afford the title compound as a pale yellow liquid (77.9 g, 288 mmol, 78 %). MS (ES+): 271 (M(C10H13F3O5^H)+.
With sulfuric acid; sodium; STEP A: Ethyl 5,5,5-trifluoro-4-oxo-3-ethoxycarbonyl-pentanoate 200 g of <strong>[123-25-1]diethyl succinate</strong> and 82 g of ethyl trifluoroacetate were mixed together and 13.2 g of sodium and 200 ml of ether were added over 5 minutes. The reaction medium was heated for 18 hours at 80 C., and then poured into 200 ml of iced 10N sulfuric acid. After decanting, drying and concentrating, the expected product was obtained which was used as is for the following step.
Reference： [1]Patent: WO2008/74752,2008,A2 .Location in patent: Page/Page column 33
[2]Beilstein Journal of Organic Chemistry,2014,vol. 10,p. 2844 - 2857
[3]Justus Liebigs Annalen der Chemie,1968,vol. 720,p. 81 - 97
[4]Journal of the Chemical Society. Perkin transactions II,1984,p. 1907 - 1916
[5]Patent: US5064861,1991,A

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