Category: esters-buliding-blocks

Some common heterocyclic compound, 22035-53-6, name is Dimethyl isopropylidenemalonate, molecular formula is C8H12O4, 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. Computed Properties of C8H12O4

A mixture of 26. 4 grams (0.15 mol) of dimethyl isopropylidenemalonate and 27.5 grams (0.15 mol) of n-bromosuccinimide were stirred in 150 mL carbon tetrachloride containing 1.0 grams benzoyl peroxide. The mixture was refluxed for 16 hours under nitrogen. The reaction was cooled in ice and the succinimide was filtered off and washed with carbon tetrachloride. The solvent was removed under reduced pressure to yield 41.3 grams of impure bromomethyl methyl isopropylidenemalonate as an oil which was used without 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 22035-53-6, its application will become more common.

Reference:
Patent; EASTMAN KODAK COMPANY; EP608582; (1994); A2;,
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Related Products of 849758-12-9,Some common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

A mixture of 4-bromo-3-fluoro-benzoic acid methyl ester (10 g, 43 mmol), bis(pinacolato)diboron (13.7 g, 54 mmol) and potassium acetate (12.7 g, 129 mmol) in dimethylsulfoxide (100 ml) was purged with argon, followed by addition of [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) (3.5 g, 4.3 mmol). The mixture was heated at 80 C. for 3 h. After this time the mixture was cooled to 25 C., washed with water, extracted with ethyl acetate and concentrated. The resulting black oil was redissolved in ethyl acetate:hexanes 1:2 and filtered through a short pad of silica gel (silica gel from QingDao, 200-300 mesh, glass column from Shanghai SD company). The filterate was concentrated in vacuo to afford 3-fluoro-4-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-benzoic acid methyl ester (12 g, 99%) as a solid which was used in the next step without further purification.

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Berthel, Steven Joseph; Chen, Li; Corbett, Wendy Lea; Feng, LiChun; Haynes, Nancy-Ellen; Kester, Robert Francis; So, Sung-Sau; Tilley, Jefferson Wright; US2011/144105; (2011); A1;,
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Reference of 5941-55-9, 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 5941-55-9 as follows.

Preparation Example 21 Synthesis of 6-cyano-2-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one (intermediate) Eight (8) grams of 2-amino-5-heptylthio-1,3,4-thiadiazole, 5 g of ethyl 3-ethoxy-2-propenoate, 10 g of polyphosphoric acid and 10 ml of xylene were mixed, and the mixture was vigorously agitated at 125C for 30 minutes. After the reaction was finished, the reaction mixture was extracted with water and toluene. The organic layer was washed with a sodium hydrogen carbonate aqueous solution and then with water. The solvent was distilled off and the residue was recrystallized from a n-hexane/ethanol mixture and thus 7.4 g of 2-heptylthio-5H-1,3,4-thiadiazolo[3,2-a]pyrimidin-5-one was obtained. Yield 75%.

According to the analysis of related databases, 5941-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; KUMIAI CHEMICAL INDUSTRY CO., LTD.; IHARA CHEMICAL INDUSTRY Co., Ltd.; EP282635; (1989); A3;,
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Electric Literature of 816-27-3, 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. 816-27-3, name is Ethyl 2-ethoxy-2-iminoacetate, This compound has unique chemical properties. The synthetic route is as follows.

A mixture of 3-aminopyridine-4-sulfonamide (112) (500 mg, 2.89 mmol), ethyl 2-ethoxy-2- iminoacetate (629 mg, 4.34 mmol) and DBU (879 mg, 5.78 mmol) in EtOH (10 mL) was heated in a microwave at 135 C for 30 min then allowed to cool to r.t.. The mixture was concentrated and the residue was dissolved in water, acidified to pH 2 with 1 M aqueous HCI and extracted with EtOAc. The organic layer was washed with water and brine, dried over Na2S04, filtered, concentrated and the residue was purified by preparative TLC (MeOH/DCM = 1 :20) to give the product (50 mg, 7% yield) as a yellow solid. LCMS (ES- API): Rt 0.51 min; m/z 255.9 [M+H] +. 1 H NMR (400 MHz, d6-DMSO) delta 13.2 (brs, 1H), 9.09 (s, 1H), 8.81 (d, J = 5.2 Hz, 1H), 7.88 (d, J =5.2 Hz, 1H), 4.42 (t, J = 7.2 Hz, 2H), 1.37 (t, J = 7.2 Hz, 3H).

The chemical industry reduces the impact on the environment during synthesis Ethyl 2-ethoxy-2-iminoacetate. I believe this compound will play a more active role in future production and life.

Reference:
Patent; CTXT PTY LIMITED; MORROW, Benjamin Joseph; FOITZIK, Richard Charles; CAMERINO, Michelle Ang; LAGIAKOS, Helen Rachel; WALKER, Scott Raymond; BOZIKIS, Ylva Elisabet Bergman; STEVENSON, Graeme Irvine; CUZZUPE, Anthony Nicholas; STUPPLE, Paul Anthony; (313 pag.)WO2019/43139; (2019); A1;,
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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. 6290-49-9, name is Methyl 2-methoxyacetate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Methyl 2-methoxyacetate

Example 23Hydrogenation of methyl methoxyacetate was carried out according to the following reaction scheme. Methyl methoxyacetate (5.0 mmol), the complex 1a (0.01 mmol), sodium methoxide (0.2 mmol), and methanol (4 mL) were added to a 100 mL autoclave equipped with a stirrer, and the hydrogenation was carried out at 80 C. for 8 hrs with hydrogen pressure of 5 MPa. As a result of the analysis of the reaction for the reaction solution according to gas chromatography, it was found that the reaction conversion rate was 100% and the selectivity was 100%.

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 6290-49-9.

Reference:
Patent; Takasago International Corporation; US2011/237814; (2011); 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. 51122-91-9, name is Dimethyl Isopropylmalonate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 51122-91-9

Step (b): After completion of the step (a), the system was cooled to 65 to 95C, and 28% CH3ONa in methanol (50.1 g) was dropwise added thereto, and then the methanol and toluene were distilled off in the same manner as in the step (a). The heating was stopped when the methanol content of the distillate became 0.01% or below by GC analysis. After the system was cooled to 95 to 105C, (1E)-1,3-dichloro-1-propene (32.1 g) in toluene was added thereto (here, the amount of the toluene was adjusted to be an amount where the mixed ratio of sulfolane and toluene as solvents in the step (b) would be 1/1 (volume ratio), considering the amount removed in the step (a)). Then, the system was heated with stirring for 2 hours, and the production of dimethyl 2-[(2E)-3-chloro-2-propenyl]-2-isopropyl malonate was confirmed by GC analysis. After the system was left to cool to room temperature, the product was added to water (210 g) at 40C or lower. Liquid separation was carried out to remove waste water (285.6 g). The organic layer was washed with a 7% sodium chloride aqueous solution (117.6 g) to remove waste water (128.2 g). Under reduced pressure, concentration was carried out at 70C or lower to obtain 130 g of the desired product in the step (b).

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 51122-91-9.

Reference:
Patent; Asahi Glass Company, Limited; EP1801094; (2007); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 849758-12-9, A common heterocyclic compound, 849758-12-9, name is Methyl 4-bromo-3-fluorobenzoate, molecular formula is C8H6BrFO2, 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.

The 4-Bromo-3-fluorobenzoic acid methyl ester (700mg; 2. 45MMOL) was dissolved in acetonitrile (3. 0ML) and placed into a 2ml microwave vessel. To the solution was added 1.5 eq OF BIS (PINACOLATO) diboron (3. 67mmol ; 1. 08G). The mixture was stirred on a magnetic stir plate until dissolution. To the mixture was added KOAC (7. 33mmol ; 7. 16MG) and 60MG of [1,1′-Bis (DIPHENYLPHOSPHINO) FERROCENE] DICHLOROPALLADIUM (II) (0. 03MOL%). The reaction mixture was heated at 160C for 2 X 600S. AFTER completion (monitored by LC- MS), the acetonitrile was evaporated to give A black solid. The solid was dissolved in EtOAc and washed with water, brine and dried over MgSO4. After filtration, the solvent was evaporated under vacuum. The solid material was then dissolved in chloroform and filtered through silica. The chloroform was evaporated to give A dark green solid (used as crude for the next reaction).

The synthetic route of 849758-12-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RENOVIS, INC.; WO2005/32493; (2005); A2;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 59247-47-1, The chemical industry reduces the impact on the environment during synthesis 59247-47-1, name is tert-Butyl 4-bromobenzoate, I believe this compound will play a more active role in future production and life.

To a mixture of /er.-butyl 4- bromobenzoate (10.1 g, 39.2 mmol), K3PO4 (20.2 g, 95.0 mmol), and dimethyl malonate (4.50 mL, 39.2 mmol) was added toluene (69 mL), Pd2(dba)3 (975 mg, 1.08 mmol), and P(fert-Bu)3 (12.8 mL, 10percent wt. in hexanes, 4.3 mmol). The reaction mixture was degassed and heated to 85°C. After 2 d, the reaction mixture was diluted with ethyl acetate, washed with water (1 x), brine (1 x), dried over MgSO4, filtered, and concentrated. Purification by flash column chromatography on silica gel (5percent to 20percent ethyl acetate in hexanes) gave dimethyl [4-(*erf-butoxycarbonyl)phenyl]malonate as a low melting white solid: 1H NMR (600 MHz, CDCl3) delta 7.98 (d, J= 8.5 Hz, 2H), 7.45 (d, J= 8.2 Hz, 2H), 4.70 (s, IH), 3.76 (s, 6H), 1.58 (s, 9H); ESIMS calcd 331.1 (M+ + Na), found 331.1 (M+ + Na).

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

Reference:
Patent; MERCK & CO., INC.; WO2007/87129; (2007); A2;,
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. 5941-55-9, name is Ethyl (E)-3-Ethoxyacrylate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl (E)-3-Ethoxyacrylate

To a mixture of 19 (3.7 g, 21.9 mmol) and (E)-ethyl 3-ethoxyacrylate (4.7 g, 32.8 mmol) in DMF (76 mL) was added Cs2CO3 (10.7 g, 32.8 mmol) and the reaction was heated at 110 C for 15 hours. After cooling to ambient temperature, the solvent was removed in vacuo and the residue was washed with acetic acid to pH 4 and extracted with EA (100 ml) for three times. The extract was dried over Na2SO4. The crude product was purified by flash chromatography to afford the title compound (2.2 g, 45.9 %). 1H NMR (400 MHz, CDCl3) delta 9.56 (br, 1H), 8.01 (d, J = 8.0 Hz, 1H), 6.08 (d, J = 8.0 Hz, 1H), 4.37 (q, J = 7.2 Hz, 2H), 2.50 (s, 1H), 1.39 (t, J = 7.2 Hz, 3H). MS (ESI) m/z 222 [M+H]+.

According to the analysis of related databases, 5941-55-9, the application of this compound in the production field has become more and more popular.

Reference:
Article; Lu, Xiaoyun; Tang, Jian; Liu, Zhiyong; Li, Minke; Zhang, Tianyu; Zhang, Xiantao; Ding, Ke; Bioorganic and Medicinal Chemistry Letters; vol. 26; 24; (2016); p. 5916 – 5919;,
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Electric Literature of 178312-47-5, A common heterocyclic compound, 178312-47-5, name is Ethyl 4,4-difluorocyclohexanecarboxylate, molecular formula is C9H14F2O2, 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 1; 4,4-Difluorocyclohexanecarboxamide A suspension of ethyl 4,4-difluorocyclohexanecarboxylate (2500 mg, 13 mmol) in ammonium hydroxide (28%, 50 ml) was stirred at 60 C. overnight. After removal of solvent, the residue was washed with water. The precipitate was obtained as product (white solid, 800 mg). 1H NMR (300 MHz, CDCl3): delta 5.31-5.45 (br, 2H), 2.02-2.27 (m, 3H), 1.92-2.02 (m, 2H), 1.72-1.87 (m, 4H). The mother liquor was acidified with 1N HCl to pH<1. The compound was extracted with EtOAc. The organic layer was washed with water, brine, dried over anhydrous sodium sulphate, filtered, condensed. 4,4-difluorocyclohexanecarboxylic acid was obtained as a 1200 mg of white solid which was further converted to 4,4-difluorocyclohexanecarboxamide by following procedure. The synthetic route of 178312-47-5 has been constantly updated, and we look forward to future research findings. Reference:
Patent; AstraZeneca AB; US2009/111830; (2009); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics