Category: esters-buliding-blocks

Application of 26759-46-6, 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. 26759-46-6, name is Methyl 2-amino-4,5-dimethoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

General procedure: 1.5 equiv of PMBONH3+Cl- plus 4.5 equiv of LiHMDS (at 0 °C for 2 h) or 4.1 equiv of LDA (from -78 °C to -10 °C, 0.5 h); yields were similar.

The synthetic route of Methyl 2-amino-4,5-dimethoxybenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; Bosch, Llui?s; Mouscadet, Jean-Franois; Ni, Xio-Ju; Vilarrasa, Jaume; Tetrahedron Letters; vol. 52; 7; (2011); p. 753 – 756;,
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Electric Literature of 135908-33-7, 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. 135908-33-7 name is Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, 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.

Example 874-{[N-cyano-2-methyl-2-phenoxypropanimidoyl]amino}bicyclo[2.2.2]octane-1-carboxylic acidEthyl N-cyano-2-methyl-2-phenoxypropanimidoate (CI-1) (1 mmol) and methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate (BA-2) (1 mmol) were mixed, and the neat mixture was heated to 100 C. under nitrogen and stirred for 5 hours. After cooling, the mixture was purified by column chromatography on silica gel (mobile phase:CH2Cl2/CH3OH=50/1) to give an impure ester product which was dissolved in methanol (10 mL). To the solution was added a solution of LiOH (10 mg) in methanol (40 mL) and water (1 mL). The mixture was refluxed overnight. After removal of the solvent, the residue was dissolved in water and adjusted pH=56 with HCl (1 mol/L), extracted with ethyl acetate (50 mL×3). The combined extracts were washed with brine, dried over sodium sulfate and concentrated. The residue was purified by preparative reverse phase HPLC [Waters 2767; Benetnach 10-C18 20×250 mm, 10 mum; 35-60% acetonitrile/water (0.05% trifluoroacetic acid), 30 mL/minute; detection at 214 and 254 nm] to give the titled compound.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 4-aminobicyclo[2.2.2]octane-1-carboxylate, and friends who are interested can also refer to it.

Reference:
Patent; ABBOTT LABORATORIES; US2010/267738; (2010); A1;,
Ester – Wikipedia,
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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. 4224-69-5, name is Methyl 2-(bromomethyl)acrylate, A new synthetic method of this compound is introduced below., Computed Properties of C5H7BrO2

General procedure: To a 20 mL two-necked round-bottom flask attached with areflux condenser were added V-65 (25 mg, 0.1 mmol) and K2CO3(138 mg, 1.0 mmol), and this flask was purged with argon.Then, 1-nonanal (1a, 71 mg, 0.5 mmol), methyl 2-(bromomethyl)acrylate (2a, 269 mg, 1.5 mmol), and degassedbenzene (5 mL) were added. The mixture was stirred at 60 C for1 h. The reaction mixture was filtered through a short plug ofCelite, and the filtrate was concentrated under reduced pressure.The residue was purified by flash column chromatographyon SiO2 (hexane/EtOAc = 1:0 to 30:1) and preparative HPLC(chloroform) to give methyl 2-methylene-4-oxododecanoate(3b, 101 mg, 84%).

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:
Article; Kippo, Takashi; Kimura, Yuki; Ueda, Mitsuhiro; Fukuyama, Takahide; Ryu, Ilhyong; Synlett; vol. 28; 14; (2017); p. 1733 – 1737;,
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Some common heterocyclic compound, 40546-94-9, name is 6-Methyl-4-phenylchroman-2-one, molecular formula is C16H14O2, 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. Application In Synthesis of 6-Methyl-4-phenylchroman-2-one

Sodium borohydride (0.76 g, 20 mmol) is added in small portions to the cooled solution of 7-methyl-4-phenyl-3,4-dihydrocoumarin (compound of formula I) (0.48 g, 2 mmol) in 20 ml of methanol. The reaction mixture is stirred for 1 h at 0 C and 4 h at room temperature. The reaction mixture is poured into 1 mol/l solution of hydrochloric acid (120 ml) and extracted with ethyl acetate (3 x 70 ml). The combined organic fractions are dried over anhydrous magnesium sulphate and the solvent evaporated to give the product in 70 % yield (0.49 g).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 40546-94-9, its application will become more common.

Reference:
Patent; LEK PHARMACEUTICALS D.D.; WO2006/66931; (2006); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 454-31-9, name is Ethyl 2,2-difluoroacetate, 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 454-31-9, SDS of cas: 454-31-9

Intermediate 6 (53.35 g, 0.22 mol) was stirred in toluene (1500 mL) at 0 C under N2. Potassium tert-butoxide (34.14 g) was added at 0-5 C and 2,2-difluoro-acetic acid ethyl ester (33.01 g, 0.27 mol) was added dropwise at 0-5 C. The RIVI was stirred at RT for 2 h, then washed with 10% H2S04 in water and the OL was dried on MgSO4,filtered and evaporated, yielding intermediate 7 (70.50 g, quantitative).

If you are interested in these compounds, you can also browse my other articles.Thank you for taking the time to read this article. I hope you enjoyed it.

Reference:
Patent; JANSSEN PHARMACEUTICA NV; VAN ROOSBROECK, Yves, Emiel, Maria; VAN DEN KEYBUS, Frans, Alfons, Maria; VELTER, Adriana, Ingrid; BUIJNSTERS, Peter, Jacobus, Johannes, Antonius; TRESADERN, Gary, John; GIJSEN, Henricus, Jacobus, Maria; (76 pag.)WO2018/83101; (2018); A1;,
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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 64123-77-9 as follows. name: Methyl 2-(3-fluorophenyl)acetate

Methyl 2-(3-fluorophenyl)acetate (1.90 g, 1 1.3 mmol) and N-bromo succinimide (2.01 g, 1 1.3 mmol) were dissolved in CC14 (80 ml). HBr (64 ul,0.56 mmol) was added and the mixture was stirred under reflux overnight. The mixture was cooled at room temperature, diluted with DCM and washed with sat. NaHCO3, water and brine. The organic layer was dried (Na2SO4), filtered and evaporated obtaining intermediate 115 (2.68 g, 96% yield).

According to the analysis of related databases, 64123-77-9, the application of this compound in the production field has become more and more popular.

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; AMARI, Gabriele; RICCABONI, Mauro; WO2011/160919; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 924-99-2,Some common heterocyclic compound, 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, molecular formula is C7H13NO2, 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.

General procedure: The substituted benzoyl chloride (18.1 mmol), 3-(N,N-dimethylamino)acrylic acid ethyl ester (18.1 mmol), triethylamine (27.1 mmol) was dissolved in 30 mL of toluene, stirred at 90 C for 4 h, concentrated and column chromatographed to give Intermediate 1. ethyl 2-(2,4-difluorobenzoyl)-3-(dimethylamino)acrylate (R2=H): yield 65%

The synthetic route of 924-99-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Fudan University; Chen, Fen Er; He, Qiuqin; Mao, Tianqi; Wan, Zhengyong; (17 pag.)CN103965163; (2016); B;,
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Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 35613-44-6, name is Methyl 2-(2-aminophenyl)acetate, 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 35613-44-6, name: Methyl 2-(2-aminophenyl)acetate

Preparation of tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1 -carboxylate (Compound 11-4) [00270j A mixture of methyl 2-(2-aminophenyl)acetate (Compound 11-3, 3.30 g, 20 mmol), tert-butyl 4-oxopiperidine-1-carboxylate (4.38 g, 22 mmol), acetic acid (HOAc, 600 mg, 10 mmol) in dichloromethane (DCM, 80 mL) was stirred at room temperature for 2 h, then sodium triacetoxyborohydride (NaBH(OAc)3, 6.36 g, 30 mmol) was added in portions and heated to 40C, stirred overnight. The reaction mixture was cooled to room temperature and diluted with dichloromethane (DCM, 200 mL), washed with water (200 mL x 2) and sodium bicarbonate (sat. aq., 200 mL x 2), dried over anhydrous sodium sulfate, concentrated to give the crude product, purified by flash colunm chromatography on silica gel (ethyl acetate petroleum ether, 1 20-1 15-1 10 v v) to give the desired product tert-butyl 4-(2-oxoindolin- 1 -yl)piperidine- 1- carboxylate (Compound 11-4, 2.65 g, yield: 42%) as a pale yellow solid. MS (ESI):mlz: 261[M+H-56]. ?H NMR (400 MHz, CDC13) oe: 7.24 (m, 2H), 7.01 (m, 2H), 4.41 (m, 1H), 4.28 (br s, 2H), 3.53 (s, 2H), 2.83 (br s, 2H), 2.32 (m, 2H), 1.70 (m, 2H), 1.50 (s, 9H).

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

Reference:
Patent; FANG, Qun, Kevin; SPEAR, Kerry, L.; CAMPBELL, Una; WO2014/106238; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Related Products of 6232-12-8, 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. 6232-12-8, name is Ethyl 4-(aminomethyl)benzoate hydrochloride, This compound has unique chemical properties. The synthetic route is as follows.

To a mixture of compound 33c (600 mg, 2.24 mmol) in THF(6.0 mL) were added oxalyl chloride (0.590 mL, 6.72 mmol) andN,N-dimethylformamide (1 drop). After being stirred for 1 h atroom temperature, the mixture was concentrated in vacuo. Theresidue was resuspended in THF (6.0 mL), and to the mixture wereadded ethyl 4-(aminomethyl)benzoate hydrochloride (965 mg,4.48 mmol) and triethylamine (1.20 mL, 8.96 mmol). After beingstirred for 12 h at room temperature, the mixture was concentratedin vacuo. The residue was taken up in ethyl acetate, washedwith 1 M hydrochloric acid (2), saturated sodium hydrogen carbonatesolution, 1 M hydrochloric acid, brine, dried over Na2SO4and concentrated in vacuo. The residue was crystallized from ethylacetate to give 34b (771 mg, 80%) as a white powder. mp 227-228 C. 1H NMR (300 MHz, DMSO-d6) d 1.31 (3H, t, J = 6.2 Hz),1.36 (3H, t, J = 6.2 Hz), 4.31 (2H, q, J = 7.1 Hz), 4.40 (2H, q,J = 7.1 Hz), 4.65 (2H, d, J = 5.5 Hz), 7.50 (2H, d, J = 8.5 Hz), 7.93(2H, d, J = 8.5 Hz), 8.57 (1H, s), 11.3 (1H, s), 13.5 (1H, s). Anal. Calcdfor C20H19N3O6S0.20H2O: C, 55.47; H, 4.52; N, 9.70. Found: C,55.50; H, 4.39; N, 9.73.

The chemical industry reduces the impact on the environment during synthesis Ethyl 4-(aminomethyl)benzoate hydrochloride. I believe this compound will play a more active role in future production and life.

Reference:
Article; Nara, Hiroshi; Sato, Kenjiro; Naito, Takako; Mototani, Hideyuki; Oki, Hideyuki; Yamamoto, Yoshio; Kuno, Haruhiko; Santou, Takashi; Kanzaki, Naoyuki; Terauchi, Jun; Uchikawa, Osamu; Kori, Masakuni; Bioorganic and Medicinal Chemistry; vol. 22; 19; (2014); p. 5487 – 5505;,
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These common heterocyclic compound, 7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, 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. Computed Properties of C6H6N2O4

General procedure: To a solution of diazo compound 1 (0.5 mmol) and alkynes (1.1 mmol) in toluene (2 mL) was added rhodium(II) pivalate (0.01 mmol). The reaction mixture was stirred at 60C for 0.5-5 h. The solvent was evaporated in rotary evaporator under reduced pressure to give the residue. The residue was purified by flash column chromatography on silica gel to give the product. 4.2.1. 2,4-Diphenyl-6H-furo[2,3-b]pyran-6-one (4). Reaction of 1 (85 mg, 0.5 mmol) and phenylacetylene (112 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 4 (86 mg, 60%) as a solid: mp 88-90 C; 1H NMR (300 MHz, CDCl3) delta 7.64-7.62 (4H, m), 7.55-7.52 (3H, m), 7.39 (2H, t, J=7.5 Hz), 7.30 (1H, d, J=7.5 Hz), 6.87 (1H, s), 6.21 (1H, s); 13C NMR (75 MHz, CDCl3) delta 159.6, 159.1, 154.0, 148.7, 135.3, 131.0, 129.4, 129.1, 128.5, 127.7, 123.7, 105.0, 101.0, 99.9; IR (KBr) 1724, 1607, 1526, 1379, 1295, 1195, 826, 761, 687 cm-1; HRMS m/z (M+) calcd for C19H12O3: 288.0786. Foud: 288.0790.

The synthetic route of 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione has been constantly updated, and we look forward to future research findings.

Reference:
Article; Somai Magar, Krishna Bahadur; Lee, Yong Rok; Kim, Sung Hong; Tetrahedron; vol. 69; 44; (2013); p. 9294 – 9302;,
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Ester – an overview | ScienceDirect Topics