Category: 25597-16-4

25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. category: esters-buliding-blocks

[0511] 5-Chlorosalicylaldehyde (20.02 g, 0.128 mole) and ethyl 4,4, 4-trifluorocrotonate (23.68 g, 0.14 mole) were dissolved in anhydrous DMF, warmed to 60 C and treated with anhydrous K2CO3 (17.75 g, 0. 128 mole). The solution was maintained at 60 C for 20 hours, cooled to room temperature, and diluted with water. The solution was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous MGS04, filtered and concentrated in vacuo to afford 54.32 g of an oil. The oil was dissolved in 250 mL of methanol and 100 mL of water, whereupon a white solid formed that was isolated by filtration. The resulting solid was washed with water and dried in vacuo, to afford the ester as a yellow solid (24.31 g, 62%): mp 62-64 C. 1H NMR (CDC13/90 MHz) 7.64 (s, 1H), 7.30-7. 21 (m, 2H), 6.96 (d, 1H, J= Hz), 5.70 (q, 1H, J= Hz), 4.30 (q, 2H, J= 7.2 Hz), 1.35 (t, 3H, J=7.2 Hz).

The synthetic route of 25597-16-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 25597-16-4, SDS of cas: 25597-16-4

[0319] A mixture of 4-benzyl-2-hydroxy-3-methylbenzaldehyde prepared as in Step 4 (1.07 g, 4.73 mmole), K2C03 (0.654 g, 4.73 mmole) and ethyl 444-trifluocrotonate (484 uL, 5.67 mmole) in anhydrous DMF (5.0 mL) was heated to 85 C under a dry N2 atmosphere for 2.75 h. The mixture was then cooled, poured into IN HC1 (100 ml) and extracted with EtOAc (2 X 100 mL). The combined extracts were washed with brine (100 mL), dried over MGS04, filtered and concentrated in vacuo to give 1.86 g of a yellow oil. The crude product was purified by silica chromatography (95: 5 hexanes: EtOAc) to give 1.04 g (59% yield) of the product as a light yellow oil: EIHRMS NILZ 376. 1310 (M+, C21H19F3O3, Calc’d 376.1286).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 25597-16-4, Each compound has different characteristics, and only by selecting the characteristics of the compound suitable for a specific situation can the compound be applied on a large scale. 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, This compound has unique chemical properties. The synthetic route is as follows.

Bromine (18.4 mL, 357 mmol) was added dropwise over 30 minutes to a solution of (E)-ethyl 4,4,4-trifluorobut-2-enoate (50 g, 297 mmol) in carbon tetrachloride (50 mL) at room temperature under nitrogen. The resulting dark red solution was refluxed for 4 hours. Additional bromine (2 ml) was added and heating was continued until the HPLC analysis showed that the starting material had been consumed. The reaction mixture was concentrated under reduced pressure to give light brown oil. HPLC (XBridge 5mu CI 8 4.6×50 mm, 4 mL/min, solvent A: 10% MeOH/water with 0.2% H3PO4, solvent B: 90% MeOH/water with 0.2% H3PO4, gradient with 0-100% B over 4 minutes): 2.96 and 3.19 minutes.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4,4,4-trifluorocrotonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; CHERNEY, Robert J.; WANG, Zhongyu; WO2012/61459; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 25597-16-4, In the chemical reaction process, reaction time, type of solvent, can easily affect the result of the reaction, thereby determining the yield and properties of the reaction product. An updated downstream synthesis route of 25597-16-4 as follows.

Step 5: ethyl 6,8-(dimethyl-D6)-2-(trifluoromethyl)-2H-chromene-3-carboxylate The resulting product (2.02 g, 0.013 mol) from step 4, ethyl 4,4,4-trifluorocrotonate (4.30 g, 0.026 mol) and anhydrous potassium carbonate (1.76 g, 0.013 mol) were dissolved in DMF (70 mL), and then the system was stirred for 6 hrs at 80 C. At the end of reaction, the reaction system was cooled to room temperature, added with water and then extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.35 g of the product (60.1%) by column chromatography. 1HNMR (400 MHz, d6-DMSO), delta ppm 7.84 (s, 1H), 7.13 (s, 1H), 7.09 (s, 1H), 5.94 (m, 1H), 4.25 (dd, 1H), 1.27 (t, 3H)

According to the analysis of related databases, 25597-16-4, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Guangzhou Institutes of Biomedicine and Health, Chinese Academy of Sciences; Zhang, Yanmei; Talley, John Jeffrey; Obukowicz, Mark G.; Tu, Zhengchao; Tortorella, Micky; Wang, Yican; Liu, Jianqi; Chen, Yan; Liu, Xiaorong; Lu, Xin; US2015/133538; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 25597-16-4, category: esters-buliding-blocks

The resulting product (2.02g, 0.013mol) from step 4, ethyl 4,4,4-trifluorocrotonate (4.30g, 0.026mol) and anhydrous potassium carbonate (1.76g, 0.013mol) were dissolved in DMF (70mL), and then the system was stirred for 6hrs at 80C. At the end of reaction, the reaction system was cooled to room temperature, added with water and then extracted with ethyl acetate, and the organic phase was dried and evaporated in vacuum to obtain 2.35g of the product (60.1 %) by column chromatography. 1HNMR(400MHz, d6-DMSO), deltappm 7.84(s,1H), 7.13(s,1H), 7.09(s,1H), 5.94(m,1H), 4.25(dd,1 H), 1.27(t,3H)

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; Guangzhou Institute Of Biomedicine And Health, Chinese Academy Of Sciences; ZHANG, Yanmei; TALLEY, John Jeffrey; OBUKOWICZ, Mark G.; TU, Zhengchao; TORTORELLA, Micky; WANG, Yican; LIU, Jianqi; CHEN, Yan; LIU, Xiaorong; LU, Xin; EP2845854; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 25597-16-4, These common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, its traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[0530] To a solution of 3-CHLORO-6-HYDROXY-2, 4-dimethylbenzaldehyde (6.9 g, 37.4 mmol) in 80 mL of DMF was added dried finely powdered K2CO3 (11.36 g, 82.2 mmol). With mechanical stirring, the reaction was heated to 65 C. To the suspension was added dropwise ethyl trifluorocrotonate (7.54 g, 44.9 mmol). The stirring reaction was heated at 90 C for 1.5 h. K2C03 was filtered from the cooled reaction. From the reaction under vacuum, DMF was removed. The resulting residue was dissolved in 400 mL EtOAc. The organic solution was washed with 100 mL 1 M KHS04, 70 mL OF SATD. KHC03, 100 mL brine, followed by drying over MGS04, and concentrating under vacuum. The crude desired product (13.8 g) of was isolated. After employing flash chromatography conditions, pure compound (9.8 g, 78 %) of was isolated and its structure confirmed by NMR and LC-MS.

Statistics shows that Ethyl 4,4,4-trifluorocrotonate is playing an increasingly important role. we look forward to future research findings about 25597-16-4.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 25597-16-4, The chemical industry reduces the impact on the environment during synthesis 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, I believe this compound will play a more active role in future production and life.

EXAMPLE 14 STR89 Step A: Preparation of 4,4,4-Trifluorocrotonic acid A solution of ethyl 4,4,4-trifluorocrotonate (9.85g, 65.9 mmole) and 1N NaOH (92.3 mL, 92.3 mmole) in THF (24 mL) was stirred at room temperature for 3 hours. The pH was brought to 1 with conc. HCl and the mixture extracted with Et2 O (3*). The combined extracts were dried (MgSO4) and concentrated in vacuo to afford the title compound as an oil. NMR (CDCl3): delta 6.55 (d, 1H); 6.89 (dq, 1H).

In the field of chemistry, the synthetic routes of compounds are constantly being developed and updated. I will also mention this compound in other articles, Ethyl 4,4,4-trifluorocrotonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Merck & Co., Inc.; US6048869; (2000); A;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, belongs to esters-buliding-blocks compound, can increase the reaction rate and produce products with better performance than those obtained under traditional synthetic methods. Here is a downstream synthesis route of the compound 25597-16-4, Quality Control of Ethyl 4,4,4-trifluorocrotonate

General procedure: To a solution of trifluorocrotonic acid (1.0 equiv) in DMF, was added the amino acid methyl ester hydrochloride (1.2 equiv), DIPEA (4.0 equiv), HBTU (1.2 equiv) and HOBt (1.2 equiv) in this order. The mixture was stirred overnight at room temperature under argon atmosphere. The solvent was evaporated under vacuum and the residue dissolved in ethyl acetate. The organic layer was washed with 10% citric acid aqueous solution (two times), water, 10% K2CO3aqueous solution (two times) and brine, dried over Na2SO4, filtrated and evaporated. The crude product was purified by column chromatography (EtOAc/cyclohexane: 3/7) to afford the corresponding alkene.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Ethyl 4,4,4-trifluorocrotonate, and friends who are interested can also refer to it.

Reference:
Article; Schweitzer-Chaput, Bertrand; Keita, Massaba; Milcent, Thierry; Ongeri, Sandrine; Crousse, Benoit; Tetrahedron; vol. 68; 35; (2012); p. 7028 – 7034;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 25597-16-4,Some common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

[0714] To a solution of 6.0 g (24 mmol) OF 2-HYDROXY-5-IODOBENZALDEHYDE and 5 mL (33.3 mmol) of ethyl 4,4, 4-trifluorocronate in 20 mL of dry DMF at 60 C was added potassium carbonate in one portion. The mixture was stirred at 60 C overnight. After cooling to room temperature, the solid was filtered and washed with EtOAc. The combined filtrates were diluted by addition with 300 mL EtOAc and washed with brine. The organic phase was dried over anhydrous magnesium sulfate and evaporated to afford an oil, which was further purified silica gel chromatography with EtOAc/hexane (1: 9). Concentration of the desired fractions afforded 4.7 g (49%) of a light yellow solid : H NMR (CDCL3/300 MHz) 7.65-7. 55 (m, 3H), 6.78 (d, J=8. 4Hz, 1H), 5.72 (q, J=6. 6 Hz, 1H), 4.34 (m, 2H), 1.37 (t, J=6. 9 Hz, 3H). MS (ES+) 398.9 (M+H, 100).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4,4,4-trifluorocrotonate, its application will become more common.

Reference:
Patent; PHARMACIA CORPORATION; WO2004/87686; (2004); A2;; ; Patent; PHARMACIA CORPORATION; WO2004/87687; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 25597-16-4,Some common heterocyclic compound, 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, molecular formula is C6H7F3O2, traditional synthetic route has been very mature, but the traditional synthetic route has various shortcomings, such as complicated route, low yield, poor purity, etc, below Introduce a new synthetic route.

To a solution of LiAlH4 (1.35g, 35.5mmol, 1.5equiv.) in dry Et2O (13.0mL) under argon atmosphere was added dropwise a solution of AlCl3 (2.22g, 16.6mmol, 0.7equiv.) in dry Et2O (6.5mL). After 20min of stirring at 0C, a solution of ethyl (E)-4,4,4-trifluorocrotonate (4.00g, 23.8mmol, 1.0 equiv.) in dry Et2O was added dropwise. The resulting mixture was allowed to stir at 0C for 2 h. A saturated aqueous solution of Na2SO4 was then added (Caution: very exothermic reaction). The mixture was filtrated and the solid was washed several times with Et2O. The organic layers were combined and washed with brine and dried over MgSO4. Solvent was removed by thorough distillation at atmospheric pressure to afford (E)-4,4,4-trifluorobut-2-en-1-ol (7) as a colorless oil which was used without any further purification.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Ethyl 4,4,4-trifluorocrotonate, its application will become more common.

Reference:
Article; Forcellini, Elsa; Hemelaere, Remy; Desroches, Justine; Paquin, Jean-Francois; Journal of Fluorine Chemistry; vol. 180; (2015); p. 216 – 221;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics