Esters-buliding-blocks

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. 89-91-8

To a solution of methyl 2,2-dimethoxyacetate (8.7 g, 64.9 mmol, 7.98 mL, 1 eq) in dioxane (50 mL) and H20 (50 mL) was added LiOH H20 (3.27 g, 77.8 mmol, 1.2 eq) at 0 C . After addition, the mixture was stirred at this temperature for 1 h, and then the resulting mixture was stirred at 20C for 10 h. TLC indicated that one new spot formed. The reaction mixture was diluted with NaOH aqueous solution (1 M, 80 mL), and extracted with petroleum ether (80 mL x 3). The combined aqueous layers were acidified with HC1 (6 M) aqueous solution to pH=l, and then extracted with ethyl acetate (80 mL for 3 times). The combined organic layers were dried over Na2S04, filtered and concentrated under reduced pressure to give 3.54 g of a colorless oil, which was used directly in the next step.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 89-91-8, its application will become more common.

Reference:
Patent; SIGILON THERAPEUTICS, INC.; VEISEH, Omid; HEIDEBRECHT, Richard; WOTTON, Paul, Kevin; OBERLI, Matthias; MILLER, Robert, James; (498 pag.)WO2018/67615; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 87-24-1, name is Ethyl 2-methylbenzoate, 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 87-24-1, 87-24-1

General procedure: In a glove box, add a ruthenium complex Ia (0.3 to 0.7 mg, 0.0002 to 0.001 mmol) to a 300 mL autoclave,Potassium methoxide (35-700 mg, 0.5-10 mmol), tetrahydrofuran (4-60 mL), and ester compounds (10-200 mmol).After sealing the autoclave, take it out of the glove box and fill it with 50 100atm of hydrogen.The reaction kettle was heated and stirred in an oil bath at 100 C for 10 to 336 hours.After the reaction kettle was cooled in an ice-water bath for 1.5 hours, the excess hydrogen was slowly released.The solvent was removed from the reaction solution under reduced pressure, and the residue was purified with a short silica gel column to obtain an alcohol compound. The results are shown in Table 5.

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 2-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Zhejiang Zhongke Chuangyue Pharmaceutical Co., Ltd.; Ding Kuiling; Tang Yitian; Han Zhaobin; (55 pag.)CN110357923; (2019); A;,
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Researchers who often do experiments know that organic synthesis is a process of preparing more complex target molecules from simple raw materials through one or more chemical reactions. Generally, it requires fewer steps, and cheap raw materials. 25597-16-4, name is Ethyl 4,4,4-trifluorocrotonate, A new synthetic method of this compound is introduced below., 25597-16-4

An Alternative Preparation of ethyl 3-(pyridin-2-yl)-4-(trifluoromethyl)isoxazole-5- carboxylate (IB); 1-B-l. Ethyl 2,3 -dibromo-4,4,4-trifluorobutanoate: Br 1 ,COOEtBr (1-B-l)[00110] 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 (2ml) 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 which used in the next step without purification. HPLC (XBridge 5mu Cl 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 basis of chemical reaction formula synthesis, the synthesis route is composed of some specific reactions and combined according to certain logical thinking. We look forward to the emergence of more reaction modes in the future.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; PITTS, William, J.; DYCKMAN, Alaric, J.; SPERGEL, Steven, H.; WATTERSON, Scott, Hunter; WO2010/85582; (2010); A1;,
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51760-21-5, A common compound: 51760-21-5, name is Dimethyl 5-bromoisophthalate, 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.

PREPARATION 47 3-bromo-5-(methoxycarbonyl)benzoic acid To a solution of dimethyl 5-bromoisophthalate (2.80 g, 10.25mmols) in methanol (18.5 mL) was added a solution of potassium hydroxide (0.29 g, 5.13mmols) in 3.7 mL of water. The mixture was stirred overnight under reflux. The mixture was partitioned between water and ethyl ether. The aqueous phase was extracted twice with ether. The aqueous was then acidified to acid pH with 5N HCl and was extracted three times with ethyl ether. The combined organics were washed with brine and dried over sodium sulphate. Purification by chromatography (hexane 100% to ethyl acetate 100%) gave 0.700 g (2.70 mmol, 26%) of the title compound. HPLC/MS (10 min) retention time 5.79 min LRMS: m/z 259 (M-1)

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, Dimethyl 5-bromoisophthalate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Almirall, S.A.; EP2394998; (2011); A1;,
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A common compound: 61644-18-6, name is Chloromethyl isobutyrate, 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. 61644-18-6

At room temperature,N-(3-(5-(4-Chlorophenyl)-1H-pyrrolo[2,3-b]pyridine-3-carbonyl)-2,4-difluorophenyl)-propane-1-sulfonamide (0.1g, 0.2mmol)And triethylamine (57 muL, 0.40 mmol) was dissolved in DMF (1 mL).And add to it Chloromethyl isobutyrate(34 mg, 0.25 mmol).The reaction mixture was stirred at room temperature for 16 hr and then evaporated.The residue was purified by silica gel column chromatography ( petroleum ether / ethyl acetate (v/v) = 4/1 to 3/1).The title compound was obtained as a white solid (45 mg,37.5%).

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, 61644-18-6, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; Guangdong Dongyangguang Pharmaceutical Co., Ltd.; Jiatuo Sciences Corporation; Xi Ning; Wang Tingjin; Tang Yin; Sun Mingming; Wang Qian; (74 pag.)CN103626765; (2016); B;,
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10259-22-0, 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. 10259-22-0, name is Ethyl 3-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Step alb: compound A5 (3-(3-methoxyphenyl)-N,N,2-trimethyl-3-oxopropanamide)To 2,2,6,6-tetramethylpiperidine (17.5 g, 125 mmol) in 50 ml dry THF were added dropwise 72 ml (115 mmol) of a n-buthyllithium solution in n-hexane (1.6 M) at -30C. After 30 minutes of stirring, 5.0 g (50 mmol) Nu,Nu-dimethylpropionamide (A1) (dissolved in 50 mL dry THF) were added and the mixture was cooled to -70C and stirred for 1 h at this temperature. 22.5 g (125 mmol) ethyl-3-methoxybenzoate (dissolved in 30 mL dry THF) were slowly added dropwise and the resulting mixture was stirred for another 2 h at -70C. After the mixture had been allowed to warm to RT, it was hydrolyzed by employing a diluted aqueous solution of HCI (36 mL). The mixture was then washed with diethyl ether several times. The combined organic layers were dried over MgS04. The organic solvents were evaporated under reduced pressure and the remaining residue was dried in vacuo. CC (eluent: n-hexane/ethyl acetate (1 :4)) yielded 6.5 g (55%) of A5 in form of a colorless oil.

The synthetic route of 10259-22-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; GRUeNENTHAL GMBH; BUSCHMANN, Helmut, Heinrich; HOLENZ, Joerg; WO2011/157390; (2011); A2;,
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Some common heterocyclic compound, 51329-15-8, name is Methyl 3,5-dibromobenzoate, molecular formula is C8H6Br2O2, 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. 51329-15-8

Methyl 5-bromo-2′-chlorobiphenyl-3-carboxylate and methyl 2,2″-dichloro-1,1′:3′,1″-terphenyl-5′-carboxylate Under argon, 60 mg (0.05 mmol) of tetrakis(triphenylphosphine)palladium(0) were added to 300 mg (1.02 mmol) of methyl 3,5-dibromobenzoate in 6 ml of dioxane. The mixture was heated to 110 C., and 1.0 ml (2.00 mmol) of 2 M aqueous sodium carbonate solution and 239 mg (1.53 mmol) of 2-chlorophenylboronic acid, dissolved in 1 ml of dioxane, were added successively. The mixture was then stirred at 110 C. for 1 h. For work-up, the reaction mixture was allowed to cool to RT and diluted with 20 ml of ethyl acetate and 20 ml of water. After phase separation, the aqueous phase was extracted two more times with in each case 20 ml of ethyl acetate. The combined organic phases were dried over magnesium sulfate, filtered and concentrated under reduced pressure. The residue was separated into the components by preparative HPLC [Method 19]. This gave 142 mg (43% of theory) of methyl 5-bromo-2′-chlorobiphenyl-3-carboxylate (Example 113A) and 166 mg (46% of theory) of methyl 2,2″-dichloro-1,1′:3′,1″-terphenyl-5′-carboxylate (Example 114A) as reaction products. Example 113A GC/MS [Method 20]: Rt=7.50 min; MS [ESIpos]: m/z=324 and 326 (M)+. Example 114A GC/MS [Method 20]: Rt=10.26 min; MS [ESIpos]: m/z=356 and 358 (M)+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 51329-15-8, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Furstner, Chantal; Keldenich, Joerg; Delbeck, Martina; Kolkhof, Peter; Kretschmer, Axel; Pluschkell, Ingo; Pook, Elisabeth; Schmeck, Carsten; Trubel, Hubert; US2013/190330; (2013); A1;,
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2033-24-1,Some common heterocyclic compound, 2033-24-1, name is 2,2-Dimethyl-1,3-dioxane-4,6-dione, molecular formula is C6H8O4, 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.

Meldrum’s adduct (19)2,4,5-Trifluorophenylacetic acid (500.0 gm, 2.63 mol) (18) was suspended in tetrahydrofuran (5.26 vol, 2.63 Ltr) at 25-30C and the reaction mixture was stirred for 10- 15 minutes. To this clear solution, l,r-carbonyldmidazole (1.5 eq, 639.68 gm) was charged in four lots and the reaction mixture was stirred for 2-3 hours at 25-300C. After 2- 3 hours stirring, Meldrum’s acid (1.2 eq, 454.87 gm) was charged and the reaction mixture was heated for 6 hours at 50-550C. After 6 hours heating at 50-55C, the tetrahydrofuran was distilled out completely at 50-55C under reduced pressure to give a dark yellow coloured residue. The dark yellow residue was acidified by using a 1:1 mixture of 35% hydrochloric acid : water (0.5 vol, 250.0 ml) at 0-50C. The product was extracted from the aqueous solution by using dichloromethane (3 x 5.0 vol, 3 x 2.5 Ltr). The combined dichloromethane layers were further washed with water (3 x 10.0 vol, 3 x 5.0 Ltr). After water washing, the dichloromethane was completely distilled under reduced pressure to give a dark yellow fluffy solid. The product was further washed with methanol (2.0 vol, 1.0 Ltr) at 0-50C.Molar Yield: 60-65% (505.0 gm) Chemical Purity: 98-99.5% (as measured by HPLC)

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 2033-24-1, its application will become more common.

Reference:
Patent; GENERICS [UK] LIMITED; MYLAN INDIA PRIVATE LIMITED; GORE, Vinayak Govind; GADAKAR, Maheshkumar; BHOSLE, Priyanka; SHINDE, Suresh; WO2010/131025; (2010); A1;,
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3196-15-4, A common compound: 3196-15-4, name is Methyl 2-bromobutyrate, 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.

[459] Step 1: methyl 2-{5-nitro-2-[(4-methylbenzoyl)imino]benzo[d]thiazol-3(2H)-yl}butanoate[460] To a stirred solution of 4-methyl-N-(5-nitrobenzo[d]thiazol-2-yl)benzamide (0.96 g, 3.06 mmol) prepared in Preparation 10 in N,N-dimethylformamide (30 mL), were added potassium carbonate (930 mg, 6.73 mmol) and methyl 2-bromobutyrate (0.76 mL, 6.13 mmol). The reaction mixture was stirred at 50 ? for 5 hours. The reaction mixture was and quenched with water and then extracted with ethyl acetate. The organic layer was washed with brine, dried over anhydrous magnesium sulfate, filtered, and then evaporated. The residue was purified with silica gel column chromatography (n-hexane/ethyl acetate/dichloromethane = 5/1/2) to give 830 mg of the titled compound as a yellow solid (Yield: 66%). [461] 1H NMR (CDCl3, 400 MHz) delta 8.20(m, 4H), 7.85(d, 1H), 7.30(d, 2H), 5.54(brs, 1H), 3.71(s, 3H), 2.57(m, 2H), 2.44(s, 3H), 0.94(t, 3H)

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-bromobutyrate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; YUHAN CORPORATION; HUR, Youn; KIM, Dong-Hyun; KIM, Eun-Kyung; PARK, Jin-Hwi; JOO, Jae-Eun; KANG, Ho-Woong; OH, Se-Woong; KIM, Dong-Kyun; AHN, Kyoung-Kyu; WO2013/43001; (2013); A1;,
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The chemical industry reduces the impact on the environment during synthesis 1865-29-8, name is Methyl 2-phenylacrylate, I believe this compound will play a more active role in future production and life. 1865-29-8

A solution of LiAlD4 (95 mg, 2.3 mmol) and AlCl3 (100 mg, 0.75 mmol) in THF was allowed to stir for 10 minutes before the addition of ester 16 (120 mg, 0.74 mmol) in THF. After 1.5 hours, the solution was quenched by addition of H2O, extracted with ether, and the ether extracts were dried (MgSO4) and concentrated in vacuo. The resulting oil was purified via flash column chromatography (15% EtOAc in hexane) to give the desired product 19 as a white solid (35 mg, 35%).

The chemical industry reduces the impact on the environment during synthesis 1865-29-8. I believe this compound will play a more active role in future production and life.

Reference:
Article; Richardson, Rebekah M.; Barney, Rocky J.; Wiemer, David F.; Tetrahedron Letters; vol. 53; 49; (2012); p. 6682 – 6684;,
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