Category: esters-buliding-blocks

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 541-16-2 as follows. Formula: C11H20O4

Compound 185a (3.15 g, 8.39 mmol) was dissolved in 50 mL of tetrahydrofuran,3.81 mL of tert-butoxycarboxylic anhydride (i.e., di-tert-butyl dicarbonate Boc2O, 16.78 mmol) and 100 mg of p-dimethylaminopyridine,Room temperature reaction 4h.The residue was purified by column chromatography, eluting with petroleum ether: ethyl acetate = 20: 1 (v / v) to give 3.18 g of compound 185b in 91% yield.

According to the analysis of related databases, 541-16-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Ocean University of China; Key Laboratory of Chemistry for Natural Products of Guizhou Province Chinese Academy of Sciences; Zhu, Weiming; Ma, Hongguang; Wang, Liping; Xu, Zhihong; Zhang, Yapeng; Wang, Yi; Liu, Peipei; (142 pag.)CN106083830; (2016); A;,
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Application of 174579-31-8, These common heterocyclic compound, 174579-31-8, name is tert-Butyl 2-(4-aminophenyl)acetate, 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.

Synthesis of compound 2.6. A solution of compound 2.5 (1.0 g, 3.19 mmol, 1.0 eq), tert-butyl 2-(4-aminophenyl)acetate (0.661g, 3.19 mmol, 1.00 eq) and K2C03 (1.32 g, 9.57 mmol, 3.0 eq) in DMF (10.0 mL) was heated at 90 C for 12 hours. Upon completion, the mixture was cooled to room temperature and poured into water. The product was extracted with ethyl acetate (50mL X 3). And the combined organic layers were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The crude material was purified using flash column chromatography to afford the compound 2.6 (1.10g, 71.4%) MS (ES): m/z 484.2 [M+H]+.

The synthetic route of 174579-31-8 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NIMBUS LAKSHMI, INC.; MASSE, Craig E.; GREENWOOD, Jeremy Robert; ROMERO, Donna L.; HARRIMAN, Geraldine C.; WESTER, Ronald T.; SHELLEY, Mee; KENNEDY-SMITH, Joshua Jahmil; DAHLGREN, Markus; WO2015/131080; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 154825-97-5, name is Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, 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 154825-97-5, Application In Synthesis of Methyl 2-(4-bromophenyl)-2,2-dimethylacetate

To a suspension of lithium aluminum hydride (2.95 g, 78 mmol, 2 equiv.) in THF (70 mL) at 0C was added a solution of methyl 2-(4-bromophenyl)-2-methylpropanoate (10 g, 39 mmol, 1 equiv.) in THF (60 mL) dropwise. After stirring at 0C for 1 h, the reaction was quenched sequentially with 3 mL of water, 9 mL of a 5% sodium hydroxide solution and 3 mL of water. It was filtered on a Celite pad using ether as an eluent. The solvent was evaporated and the residue was purified by bulb-to-bulb distillation (2-4 mbar, l30C) to afford 2-(4-bromophenyl)-2-methylpropan-l-ol (8.27 g, 93% yield).1H NMR: 1.30 (s, 6H), 3.57 (s, 2H), 7.25 (d, J = 8.6 Hz, 2H), 7.45 (d, J = 8.6 Hz, 2H).13C NMR: 145.6 (s), 131.4 (d, 2C), 128.2 (d, 2C), 120.1 (s), 72.8 (t), 39.9 (s), 25.2 (q,2C).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 2-(4-bromophenyl)-2,2-dimethylacetate, and friends who are interested can also refer to it.

Reference:
Patent; FIRMENICH SA; COULOMB, Julien; ODDON, Gilles; (33 pag.)WO2019/141761; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, 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 924-99-2, category: esters-buliding-blocks

A mixture of 2,4-dichloro-5-fluoro-3-nitrobenzoic acid (10.2 g, 40 mmol) and thionyl chloride (19.0 g, 160 mmol) in dry benzene (120 ml) was refluxed for 3 – 4 h under anhydrous conditions. The solvent and excess thionyl chloride were then distilled off under reduced pressure, and dry benzene (20 ml) was then introduced into the reaction vessel and re-distilled so as to remove traces of thionyl chloride. The resulting 2,4-dichloro-5-fluoro-3-nitrobenzoyl chloride, formed as thick oil, was used as such for the next step without further purification. To a stirred and cooled (5-10 C) solution of ethyl 3-(N,N-dimethylamino)acrylate (6.3 g, 44 mmol) and triethylamine (8.1 g, 80 mmol) in dry benzene (50 ml) was added dropwise a solution of the crude acid chloride (prepared above) in dry benzene (25 ml). The resulting mixture was refluxed for 2 h, then cooled to rt and washed with water (2 x 30 ml). The organic layer was separated, dried (anhydrous MgSO4) and the solvent benzene was then evaporated to dryness under reduced pressure. The residual product was soaked in methanol (10 ml) whereby the title compound 5 was produced as yellowish powder which was collected by suction filtration and dried. Yield = 13.8 g (91%). IR (KBr): v 3074, 3037, 2988, 2928, 2873, 1689, 1619, 1554, 1454, 1397, 1375, 1344, 1321, 1278, 1206, 1177, 1129, 1030 cm-1; 1H NMR (300 MHz, CDCl3): delta 0.95 (t, J = 7.1 Hz, 3H, CH3), 2.97 (s, 3H) and 3.37 (s, 3H) [N (CH3)2], 3.94 (q, J = 7.1 Hz, 2H, CH2Me), 7.27 (d, 3JH-F = 8.2 Hz, 1H, H-6), 7.91 (br s, 1 H, N-C(3″)-H); 13C NMR (75 MHz, CDCl3): delta 13.8 (CH3CH2), 43.3, 48.4 [N (CH3)2], 60.2 (CH2Me), 100.9 (C-2″), 114.5 (d, 2JC-F = 23.3 Hz, C-4), 116.9 (d, 2JC-F = 23.1 Hz, C-6), 118.2 (d, 3JC-F = 4.5 Hz, C-1), 144.2 (d, 3JC-F = 6 Hz, C-3), 148.8 (br d, 4JC-F = 1.3 Hz, C-2), 156.6 (d, 1JC-F = 254 Hz, C-5), 160.5 (N-C-3″), 166.5 (CO2Et), 185.1 (C = O).

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 3-(dimethylamino)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Universitaet Duisburg-Essen; EP2128160; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 685-88-1, name is Diethyl fluoromalonate, This compound has unique chemical properties. The synthetic route is as follows., Computed Properties of C7H11FO4

To a solution of diethyl 2- fluoromalonate (5.00 g, 28.1 mmol) in EtOH (100 mL) was added LiOH H20 (2.70 g, 64.3 mmol) at 25 C. The mixture was heated to 50 C for 16 hours. The mixture was filtered to collect solid. The filtrate was concentrated to dryness to get oil. The oil and the solid were dissolved in H20 (30 mL) and MTBE (100 mL), the mixture was acidified by adding cone. HC1 to pH 1, the aqueous layer was extracted with MTBE (30 mL x2), the combined organic layers were dried over Na2S04, filtered and concentrated to give 2-fluoromalonic acid (3.00 g, yield 88%) as a solid.

According to the analysis of related databases, 685-88-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; N30 PHARMACEUTICALS, LLC; SUN, Xicheng; QIU, Jian; STOUT, Adam; WO2012/83165; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Electric Literature of 37746-78-4, As we all know, there are many different methods for the synthesis of a compound, and people can choose the synthesis method that suits their own laboratory according to the actual situation. 37746-78-4 name is (E)-Ethyl 4-bromobut-2-enoate, This compound is widely used in many fields, so it is necessary to find a new synthetic route. The downstream synthesis method of this compound is introduced below.

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, (E)-Ethyl 4-bromobut-2-enoate, and friends who are interested can also refer to it.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

These common heterocyclic compound, 108928-00-3, name is Ethyl 2,4-difluorobenzoate, 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. SDS of cas: 108928-00-3

2,4-Difluorobenzoic acid ethyl ester (5.33g) was cooled to 0C and treated with concentrated sulfuric acid (3. 5mL) and then fuming nitric acid (3. 5mL). The mixture was stirred for 2 hours at 0C and then partitioned between dichloromethane (2x50mL) and water (25mL). The organic phase was back extracted with water (25mL) and then dried over magnesium sulfate and concentrated in vacuo. This provided the desired compound as a white solid (5. 00g) which was used without further purification.

The synthetic route of Ethyl 2,4-difluorobenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SMITHKLINE BEECHAM P.L.C.; WO2003/87098; (2003); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 1234616-21-7,Some common heterocyclic compound, 1234616-21-7, name is Methyl imidazo[1,2-b]pyridazine-6-carboxylate, molecular formula is C8H7N3O2, 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.

Synthesis of imidazo[l,2-b]pyridazin-6-ylmethanol:To a stirred solution of imidazo[l,2-b]pyridazine-6-carboxylate (3.5 g, 22.77 mmol) in MeOH:THF (45 mL, 1 :2) was added NaBH4 (1.72 g, 45.26 mmol) portion wise at 0C and stirred for 2h. After full consumption of starting material by TLC, the reaction was diluted with saturated Na2C03 solution and extracted with EtOAc. The combined organic layer was dried over sodium sulphate, filtered and concentrated in vacuo to obtain the crude product. The crude material was washed with 50%> EtOAc/Hexane to afford crude imidazo[l,2-b]pyridazin-6-ylmethanol (2.5 g). 1H-NMR (DMSO-d6, 400 MHz): delta 8.21 (s, 1H), 8.06 (d, 1H), 7.21 (s, 1H), 7.24 (d, 1H), 5.68 (br s, 1H), 4.59 (s, 2H); LC-MS: 85.80%; 149.6 (M++l) (column; X-Select C-18, (50×3.0 mm, 3.5mu); RT 0.72 min. 5mM NH4OAc in water: ACN; 0.8 ml/min); TLC: 100% EtOAc (Rf: 0.2).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl imidazo[1,2-b]pyridazine-6-carboxylate, its application will become more common.

Reference:
Patent; ENVIVO PHARMACEUTICALS, INC.; RIPKA, Amy; SHAPIRO, Gideon; MCRINER, Andrew; WO2012/40230; (2012); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Application of 89-91-8,Some common heterocyclic compound, 89-91-8, name is Methyl 2,2-dimethoxyacetate, molecular formula is C5H10O4, 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 2-chlorobenzylamine (30.0 g, 212 mmol) in MeOH (200 mL) was added triethylamine (36.7 mL, 265 mmol) and methyl dimethoxyacetate (31.0 g, 233 mmol). The reaction was heated to 80 C for 20 h. After cooling to room temperature, the reaction wasconcentrated in vacuo. EtOAc (300 ml) was added, washed with iN HC1 (300 mL x 2) and sat. aq. NaHCO3 (300 mL x 2). The organic layer was dried over anhydrous Na2SO4, filtered andconcentrated in vacuo to give the title compound (40.0 g, crude) as colorless oil that required no further purification. ?H NMR (400 IVIFIz, CDC13) 7.39 – 7.33 (m, 2H), 7.24 – 7.21 (m, 2H),4.73 (s, 1H), 4.56 (d, J 6.0 Hz, 2H), 3.38 (s, 6H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 2,2-dimethoxyacetate, its application will become more common.

Reference:
Patent; GENENTECH, INC.; CONSTELLATION PHARMACEUTICALS, INC.; CYR, Patrick; BRONNER, Sarah; ROMERO, F. Anthony; MAGNUSON, Steven; TSUI, Vickie Hsiao-Wei; MURRAY, Jeremy M.; WAI, John; LAI, Kwong Wah; WANG, Fei; CHEN, Kevin X.; (351 pag.)WO2017/205538; (2017); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Reference of 4224-69-5, In the next few decades, the world population will flourish. As the population grows rapidly and people all over the world use more and more resources, all industries must consider their environmental impact. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

(2) To an anhydrous THF solution (2 ml) of the above-obtained Compound (8) (A=-CH=CH-CH=CH-, PG=TBS, 24(E)) (48 mg, 76.8 mumol) were added zinc (powder) (8 mg, 0.12 mmol), methyl 2-(bromomethyl)acrylate (13.8 mul, 0.12 mmol) and a saturated ammonium chloride aqueous solution (0.7 ml) at 0C, and the mixture was stirred for 30 min at room temperature. The reaction was quenched with water, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and then with brine, dried over anhydrous magnesium sulfate, and concentrated. The residue was purified by column chromatography (5%?20% ethyl acetate in hexane) to obtain Compound (C) (60 mg, 107% yield). Compound (C):1H NMR (CDCl3) delta : 0.055 (s, 3 H), 0.059 (s, 3 H), 0.062 (s, 6 H), 0.55 (s, 3 H), 0.88 (s, 18 H), 1.04 (d, J=6.6 Hz, 3 H), 1.23-2.17 (m, 15 H), 2.18-2.24 (m, 1 H), 2.42-2.52 (m, 2 H), 2.60-2.65 (m, 1 H), 2.78-2.86 (m, 1 H), 3.74 (s, 3 H), 4.19-4.22 (m, 1 H), 4.28-4.34 (m, 1 H), 4.34-4.39 (m, 1 H), 4.86 (d, J=2.2 Hz, 1 H), 5.17 (s, 1 H), 5.53-5.62 (m, 1 H), 5.67 (d, J=1.2 Hz, 1 H), 5.90-6.03 (m, 2 H), 6.15-6.25 (m, 2 H), 6.26 (d, J=1.2 Hz, 1 H). MS m/z 747 (M+23)+.

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, Methyl 2-(bromomethyl)acrylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; TEIJIN LIMITED; EP1477483; (2004); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics