Esters-buliding-blocks

25542-62-5, 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. 25542-62-5, name is Ethyl 6-bromohexanoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedeure: In a 250-mL round-bottom flask, 4-hydroxybenzaldehyde (5g, 41 mmol, 1eq.) and K2CO3( 14g,101 mmol, 2.5eq) were dissolved in anhydrous DMF (25 mL). Ethyl 6-bromohexanoate (13.7g, 61 mmol, 1.5 eq.) was slowly added to the solution under nitrogen atmosphere and refluxed for 2-4 h. Reaction was monitored by TLC. The solution was filtered over Celite 535, diluted with ethyl acetate (150 mL), and washed with brine (100 mLx2). The organic phase was dried over MgSO4, filtered, and concentrated. The crude product, a colorless oil (10.66 g, 40 mmol, 99%), was used without further purification.

The synthetic route of Ethyl 6-bromohexanoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Mitachi, Katsuhiko; Salinas, Yandira G.; Connelly, Michele; Jensen, Nicholas; Ling, Taotao; Rivas, Fatima; Bioorganic and Medicinal Chemistry Letters; vol. 22; 14; (2012); p. 4536 – 4539;,
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The chemical industry reduces the impact on the environment during synthesis 61644-18-6, name is Chloromethyl isobutyrate, I believe this compound will play a more active role in future production and life. 61644-18-6

A mixture of chloromethyl 2-methylpropanoate (1.5 eq), tert-butyl hydrogen fumarate (0.5 g, 1.0 eq), and Cs2CO3 (2.0 eq) in N-methylpyrrolidone (10 mL) was stirred between 50 to 70 C. overnight. The reaction was concentrated in vacuo to a residue, diluted with ethyl acetate, and washed with water, saturated bicarbonate solution and brine. The organic phase was separated, dried over Na2SO4, filtered and concentrated in vacuo to yield the crude product. The crude material was then purified by silica gel column chromatography using ethyl acetate and hexanes to yield compound (6a).

The chemical industry reduces the impact on the environment during synthesis 61644-18-6. I believe this compound will play a more active role in future production and life.

Reference:
Patent; Nguyen, Mark Quang; (47 pag.)US2016/229819; (2016); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

42726-73-8, name is tert-Butyl methyl malonate, 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. 42726-73-8

Tert-butyl methyl malonate (2.64 g, 15.14 mmol) was dissolved in THF (50 mL). Sodium hydride (0.605 g, 15.14 mmol) was added portion-wise at 0 ¡ãC and the reaction mixture was allowed to stir for 15 mm at room temperature. 2-chloro-5-nitropyridine (2.012.61 mmol) dissolved in 10 mL of THF was then added to the mixture and the mixture was allowed to stir for 4 hours at room temperature before being quenched withsaturated aqueous ammonium chloride and extracted with EtOAc (3x). The combined organic layer was washed with brine, dried with sodium sulfate, filtered and concentrated. The resulting residue was dissolved in 30 mL of 2:1 DCMITFA and stirred for 1.5 hours. The reaction mixture was then diluted with 1.5 M potassium phosphate solution and extracted with EtOAc (3x). The combined organic layer was washed with brine, driedwith sodium sulfate, filtered and concentrated. The resulting residue was dissolved in methylene chloride before being charged to an 80 g silica gel cartridge which was eluted with a 30 mm gradient from 0-100percent EtOAc in hexane. Fractions containing the desired product were concentrated to yield Intermediate I-109A (1.06 g, 5.40 mmol, 42.8 percent yield), as a yellow oil. LC-MS: Method H, MS (ESI) m/z: 197.0 (M+H). ?H NMR(400MHz, CDC13) 9.41 (d, J=2.6 Hz, 1H), 8.49 (dd, J8.6, 2.6 Hz, 1H), 7.56 (d, J8.6 Hz, 1H), 4.02 (s, 2H), 3.78 (s, 3H).

Statistics shows that 42726-73-8 is playing an increasingly important role. we look forward to future research findings about tert-Butyl methyl malonate.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; ZHANG, Xiaojun; PRIESTLEY, Eldon Scott; BATES, J. Alex; HALPERN, Oz Scott; REZNIK, Samuel Kaye; RICHTER, Jeremy M.; (1137 pag.)WO2018/13774; (2018); A1;,
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Ester – an overview | ScienceDirect Topics

701-83-7, These common heterocyclic compound, 701-83-7, name is 3-Fluorophenyl 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.

EXAMPLE 16 Preparation of 4′-Fluoro-2′-hydroxyacetophenone m-Fluorophenyl acetate (123 g, 0.798 mol) is cooled with an ice-bath, treated portionwise with aluminum chloride (150 g, 1.12 mol), stirred at 190 C. for one hour, and cooled to obtain a solid. A mixture of ice, water and hydrochloric acid, and methylene chloride are added to the solid. The resultant mixture is stirred for several minutes, and the phases are separated. The organic phase is washed sequentially with water, saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain the title product (99.0 g) which is identified by 1H NMR spectral analysis.

Chemical properties determine the actual use. Each compound has specific chemical properties and uses. We look forward to more synthetic routes in the future to expand reaction routes of 701-83-7.

Reference:
Patent; BASF Aktiengesellschaft; US6355796; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 18927-05-4, name is Methyl 3-Methoxyphenylacetate, molecular formula is C10H12O3, 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. 18927-05-4

Methyl bromo(3-methoxyphenyl)acetate; A mixture of 15.7 g (87.1 mmol) of methyl (3-methoxyphenyl)acetate, 16.3 g (91.5 mmol) of Lambda/-bromosuccinimide and a catalytic amount of AIBN in tetrachloromethane (150 ml) was heated under reflux with stirring for 2 h. The cooled reaction solution was filtered and the solvent was removed in vacuo. Yield: 21.8 g (100%) of yellow oil 1H-NMR (DMSOd6): 3.72 (s, 3H), 3.76 (s, 3H), 5.90 (s, 1 H), 6.92-6.97 (m, 1 H), 7.08- 7.13 (m, 2H), 7.28-7.34 (m, 1 H). MS (API-ES,pos) m/z = 261 [M+H]+

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 18927-05-4, its application will become more common.

Reference:
Patent; ABBOTT GMBH & CO. KG; WO2008/25736; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Some common heterocyclic compound, 42726-73-8, name is tert-Butyl methyl malonate, molecular formula is C8H14O4, 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. 42726-73-8

Example 2; Preparation of Compound 2; Compound 1 (7 g), tert-butyl methyl malonate (6 g), 0.5 ml of piperidine and 0.3 ml of acetic acid are heated under reflux for three hours in 100 ml of methanol. After cooling to room temperature, the mixture is filtered and the filtrate is concentrated. The concentrated filtrated is poured into water, and resulted precipitate is filtered off with suction to collect the solid that is air-dried. The crude product is further purified with silica gel chromatography to yield the desired Compound 2.

The chemical industry reduces the impact on the environment during synthesis tert-Butyl methyl malonate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; AAT Bioquest, Inc.; US8318953; (2012); B2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

538-23-8, A common compound: 538-23-8, name is Propane-1,2,3-triyl trioctanoate, belongs to esters-buliding-blocks compound, it can change the direction of chemical reaction, and react with certain compounds to generate new functional products. A new synthetic method of this compound is introduced below.

Two mg of a free astaxanthin (manufactured by Sigma) and 300 mg of tricaprilin as a triglyceride form fatty acid were placed in a brown glass bottle. Three hundred mg of immobilized lipase prepared by the method described in the example of lipase immobilization was added thereto, and 30 muL of water and 12 ml of n-hexane were further added thereto and stirred fully afterwards. Thereafter, while stirring, reaction was carried out at 45C. Three days later, the reaction product was taken out. The immobilized enzyme was eliminated by decantation, and the supernatant hexane was eliminated. The composition ratio of astaxanthin was then analyzed by HPLC. As a result, the composition ratio was 64.1% astaxanthin, 23.9% monoester, and 2.3% diester.

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, Propane-1,2,3-triyl trioctanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; SUNTORY LIMITED; EP1500645; (2005); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

14062-25-0, 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 14062-25-0 as follows.

Ethyl-2-(4-bromophenyl)-2-diazoacetate (5j). To a solution of ethyl-4-bromophenylacetate (9j) (400 mg, 1.65 mmol) and 4-acetamidobenzenesulfonylazide (p-ABSA) (593 mg, 2.47 mmol) in dry CH3CN (4 mL) at 0C 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) (376 mg, 2.47 mmol) was added. The mixture was stirred at it overnight, poured onto water (30 mL) andextracted with EtOAc (3 x 30 mL). The combined organic layers were washed with brine (40 mL), dried over Na2SO4 and the solvent evaporated under reduced pressure. The residue was dissolved in C112C12 (30 mL) whereby the side product 4-acetamidobenzenesulfonamide precipitated as a white solid. The suspension was filtered through silica gel and concentrated to afford an orange solid 5j (359 mg, 81 %).

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 14062-25-0, and friends who are interested can also refer to it.

Reference:
Patent; ALLOCYTE PHARMACEUTICALS AG; BREITENSTEIN, Werner; HUERZELER, Marianne; KELLY, Terence; MANCUSO, Riccardo; SCHNEIDER, Gisbert; WEITZ-SCHMIDT, Gabriele; WO2015/189265; (2015); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 42726-73-8, name is tert-Butyl methyl malonate, 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 42726-73-8, 42726-73-8

tert-Butyl methyl malonate (3.9 mL, 23 mmol), potassium carbonate (7.9 g, 57.5 mmol) and dibromoethane (2.57 mL, 29.9 mmol) were combined in DMF (75 mL) and the resulting reaction mixture was stirred at room temperature overnight. The mixture was poured onto water (500 mL) and extracted with ether (3 X). The combined ethereal layers were washed with water, then washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. Purification by flash chromatography (0-5percent EtOAc/ hexane) provided l-(tert-butyl) 1-methyl cyclopropane-l,l-dicarboxylate (2.35 g, 51percent yield). Combined with another batch afforded the desired product (4.28 g). 1H NMR (300 MHz, Chloroform-d) delta 3.75 (s, 3H), 1.47 (s, 9H), 1.38 (s, 4H).

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, tert-Butyl methyl malonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; UNIVERSITY OF HAWAII; TURKSON, James; YUE, Peibin; TIUS, Marcus; BROTHERTON-PLEISS, Christine; LOPEZ TAPIA, Francisco, Javier; (420 pag.)WO2018/136935; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

4518-10-9,Some common heterocyclic compound, 4518-10-9, name is Methyl 3-aminobenzoate, molecular formula is C8H9NO2, 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.

EXAMPLE 13-[2-(2,4,6-Trihydroxy-phenyl)-acetylamino]-benzoic acid (18)SCLiOH H2O/TIH F EPO Step 1: (The following reaction is done in an anhydrous N2 atmosphere.) Dissolve EDC hydrochloride (122mg, 0.64mmol) and triethylamine (89muL, 0.64mmol) in anhydrous dichloromethane (3.2mL) and stir for 5min at rt. Add 2-(2,4,6-Trimethoxyphenyl)- acetic acid (14) (lOlmg, 0.45mmol) and DMAP (8mg, O.Ommol) and stir for lOmin. Add ethyl ester (15) (70mg, 0.42mmol) and stir the reaction solution overnight at rt. Hydrolize the reaction solution with saturated aqu. NH4Cl followed by water, separate layers, extract aqu. layer with dichloromethane (3 times) and wash the combined organic layers with water and brine and dry with Na2SO4. Remove solvent under reduced pressure. Purify crude product by preparative radial chromatography (silica gel 60PF, EtOAc/CyH 1+1) to obtain 3-[2- (2,4,6-Trimethoxy-phenyl)-acetylamino]-benzoic acid methyl ester (16) as a white solid (145mg, 95%). [K. C. Nicolaou; P. S. Baran; Y.-L. Zhong; K. Sugita; J Am. Chem. Soc; 2002; 124; 10; 2212-2220]. 1H NMR (400MHz, CDCl3): 3.68 (s, 2 H); 3.83 (s, 3 H); 3.84 (s, 6 H); 3.87 (s, 3 H); 6.18 (s, 2 H); 7.33 (t, 1 H, J= 8.0Hz); 7.56 (br.s, 1 H); 7.69 (br.dd, 1 H, J= 7.8Hz); 7.78 (t, 1 H, J= 1.8Hz); 7.90 (dd, I H1 J/ = 8.1Hz, J2 = 1.3Hz).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-aminobenzoate, its application will become more common.

Reference:
Patent; REVOTAR BIOPHARMACEUTICALS AG; WO2007/39112; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics