Category: esters-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 792-74-5, name is Dimethyl [1,1′-biphenyl]-4,4′-dicarboxylate, 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 792-74-5, 792-74-5

a) Preparation of 4,4′-bis (Hydroxy-Methyl) Biphenyl. 789mg (20.8 mmoles) of LiAlH4 in 150ml of anhydrous THF (tetrahydrofuran) are placed in a 2-litre flask which has a mechanical agitator, cooler, filler funnel and heating bath. A solution, heated to 50oC, of 7.5g (27.7 mmoles) of 4,4′-bis (methoxycarbonyl)biphenyl in 500ml of anhydrous THF is added dropwise, over a period of 1 hour, to the mixture, heated in an inert atmosphere to 50oC under agitation. After a further 30 minutes of agitation in a heating bath, the mixture is cooled to ambient temperature and the excess LiAlH4 is destroyed by the careful addition of 15ml of a THF/H2O (80:20) mixture. The reaction mixture is filtered on Septum G2, washing the precipitate with anydrous ethanol (3x100ml). The combined filtrate and washings are evaporated to dryness under vacuum with the heating bath at 40oC. The residue is then redissolved with 100ml of hot acetone (50oC), eliminating the insoluble residue by filtration, dried on anhydrous Na2SO4 and evaporated to dryness. 5.74g of 4,4′-bis (hydroxymethyl) biphenyl are obtained with a molar yield of 96.6percent.

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 [1,1′-biphenyl]-4,4′-dicarboxylate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ENIRICERCHE S.p.A.; EP469682; (1992); A1;,
Ester – Wikipedia,
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13831-03-3,Some common heterocyclic compound, 13831-03-3, name is tert-Butyl propiolate, molecular formula is C7H10O2, 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 9 Methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate 1-(Pyridin-3-yl)naphthalen-2-ol (80 mg, 0.26 mmol) obtained in Example 8 (1) was dissolved in dimethylformamide (2 mL), sodium hydride (16 mg, 0.4 mmol) was added thereto in an ice bath, and the solution was stirred at room temperature. After 10 minutes, methyl propiolate (91 muL, 1.1 mmol) was added to the reaction solution and the reaction solution was further stirred at 110 C. After 16 hours, water was added to the reaction solution in an ice bath, extraction was carried out using chloroform, the organic layer was dried over sodium sulfate and filtered, and then the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (ethyl acetate_hexane=1:2) to obtain a crude material of methyl (E)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate (25 mg, yield of 22%) and methyl (Z)-3-[[1-(pyridin-3-yl)naphthalen-2-yl]oxy]acrylate. j0682] A title compound (white crystal, 24 mg, yield of41%) was obtained according to the same method as inExample 9 using 4-(2-mercaptonaphthalen- 1 -yl)benzonitrile(40 mg, 0.15 mmol) obtained in Example 48 (3) and t-butylpropiolate (63 pL, 0.46 mmol).10683] ?H NMR (CDC13, 400 MHz): oe=1.43 (s, 9H), 5.46(d, 1H, J=15 Hz), 7.32 (d, 1H, J=8 Hz), 7.4-7.5 (m, 3H),7.5-7.6 (m, 2H), 7.63 (d, 1H, J=8 Hz), 7.78 (d, 2H, J=8 Hz),7.9-8.0 (m, 2H).

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

Reference:
Patent; J-Pharma Co., Ltd.; Endo, Tsuyoshi; Kobayashi, Kunio; Tanaka, Hiroto; Saito, Daisuke; Hirano, Masaharu; Endou, Hitoshi; Anzai, Naohiko; (68 pag.)US2017/290795; (2017); A1;,
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

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

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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

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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Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics