Category: esters-buliding-blocks

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. 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: Methyl 4-(benzyloxy)-3-methoxybenzoate

E) 4-Benzyloxy-3-methoxy benzoic acid; A solution of sodium hydroxide (2.0 g) in methanol (50 ml) was added to a solution of 4-benzyloxy-3-methoxy benzoic acid methyl ester (4.64 g) in methanol (50 ml) and refluxed for 4 hrs. After removal of methanol under reduced pressure the residue was dissolved in water (150 ml) and washed with ethyl acetate (2 x 50 ml). The aqueous layer was acidified with 2N hydrochloric acid to pH 2. The precipitated product was collected by filtration which on drying under vacuum provided 4.17 g of 4-benzyloxy- 3-methoxy benzoic acid. (Yield = 74%) ‘H NMR CDCl3 7.7 (1H, d, J = 8Hz) 7.63 (1H, s) 7.3-7.5 (5H, m) 6.92 (1H, d, J 8Hz) 5.25 (2H, s) 3.98 (3H, s)

According to the analysis of related databases, 56441-97-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; PROTEOTECH, INC.; WO2005/113489; (2005); A1;,
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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. 431-47-0, name is Methyl 2,2,2-trifluoroacetate, A new synthetic method of this compound is introduced below., Safety of Methyl 2,2,2-trifluoroacetate

Synthesis Example 40 Synthesis of N-propargyltrifluoroacetamide Propargylamine (Aldrich, 25 g, 0.45 mol) was added dropwise to methyl trifluoroacetate (Tokyo Chemical Industry Co., Ltd., 69.2 g, 0.54 mol) cooled to 0 C. They were allowed to react at 0 C. for two hours to afford 43.8 g (86.0%) of N-propargyltrifluoroacetamide after purification by vacuum distillation (23 mmHg, boiling point; 77 C.).

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; The Institute of Physical and Chemical Research; US6365350; (2002); B1;,
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Electric Literature of 56441-97-5, A common heterocyclic compound, 56441-97-5, name is Methyl 4-(benzyloxy)-3-methoxybenzoate, molecular formula is C16H16O4, 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.

Commercially available methyl 4-hydroxy-3-methoxy-benzoate 1 was converted in 5 steps to 4-(3-fluoroanilino)-6-methoxy-7-benzyloxy-quinazolme 15 (35% overall yield).[17,18] The only significant modification involved an improved workup of the nickel chloride hexahydrate-sodium borohydride reduction of the nitro intermediate. Debenzylation with trifluoroacetic acid to give the 7-hydroxy intermediate 16, followed by alkylation with propargyl bromide in acetonitrile, gave 13 in a 65% yield for 2 steps. This method involved an additional step, and the overall yield was greater. In addition, the final 7-hydroxy intermediate 16 could be used to generate other products [19].

The synthetic route of 56441-97-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; HANSON, Robert, N.; WO2010/85747; (2010); A1;,
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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. Recommanded Product: 924-99-2

General procedure: All microwave reactions were carried out in a capped (10 mL) microwave-vessel (Borosilicate glass vial sealed) that was placed in a microwave cavity. The pressure was set at 17 bar (average of an effective pressure = 4 bar) with power 75 W. DIEA (3.4 g, 3.4 mmol) was added to a solution of either 2,5-difluoro-4-(pyrrolidin-1-yl) benzoylchloride 12 (0.83 g, 3.4 mmol) or 2,5-difluoro-4-(pyrrolidin-1-yl)benzothioyl chloride 13 (0.88 g, 3.4 mmol) and ethyl-3-(diethylamino)acrylate 14 (0.45 g, 3.1 mmol) in acetonitrile (5 mL). The mixture reaction was held at 100 C for 20 min. After the reaction vessel was cooled to room temperature, the crude product was diluted with water (10 mL) and extracted with ethyl acetate(3 × 10 mL). The organic layers were combined, dried over Na2SO4, filtered, evaporated and purified by a flash column chromatography (eluent n-hexane: acetone, 3:1)to give the titled compounds.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 924-99-2, its application will become more common.

Reference:
Article; Almashal, Faeza A.; Alshawi, Jasim M.; Dhumad, Adil M.; Jassem, Ahmed M.; Medicinal Chemistry Research; (2020);,
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Related Products of 23680-40-2, A common heterocyclic compound, 23680-40-2, name is Methyl 3-bromopropiolate, molecular formula is C4H3BrO2, 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.

A solution of 2-methylfuran (15.7mL, 174 mmol) andmethyl 3-bromopropiolate 11 (7.10 g, 43.6 mmol) incyclohexane (100 mL) was refluxed for 1 d. Afterremoval of the solvent, the resulting mixture of 12aand 12b was used in the next step without purification.12a: 1H NMR (300 MHz, CDCl3) delta 1.89 (3H, s),3.79 (3H, s), 5.21 (1H, d, J = 1.8 Hz), 6.99 (1H, d,J = 5.1 Hz), 7.14 (1H, dd, J = 1.8, 5.1 Hz); 13C NMR(75 MHz, CDCl3) delta 16.43, 51.65, 87.98, 91.49, 142.12,146.96, 149.94, 153.89, 163.49.The ratio of 12a:12b was determined to be 11:1based on 1H NMR analysis. The signal due to 1-Me of12b was observed at delta = 1.74.

The synthetic route of 23680-40-2 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Konishi, Shunsuke; Mori, Naoki; Takikawa, Hirosato; Watanabe, Hidenori; Bioscience, Biotechnology and Biochemistry; vol. 83; 3; (2019); p. 391 – 399;,
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Some common heterocyclic compound, 14062-19-2, name is Ethyl p-Tolylacetate, molecular formula is C11H14O2, 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. Product Details of 14062-19-2

LiHMDS was prepared by the treatment of HMDS (2.432 g, 15.07 mmol) with n-BuLi (1.6 M solution in hexane, 9.4 mL, 15 mmol) in dry THF (30 mL) at 0C for 30 min. To a solution of ethyl p-tolylacetate (1.778 g, 9.98 mmol) in dry THF (30 ml) was added the LiHMDS at -78C. The mixture was stirred at -78C for 30 min. To the mixture, ethyl cyanoformate (1.110 g, 11.20 mmol) was added at -78C, and then the mixture was allowed to warm to 0C for 80 min. 10% HCl was added at 0C, and the mixture was extracted twice with CH2Cl2. The combined organic extracts were dried over Na2SO4. After removal of the solvent, the residue was purified by column chromatography using silica gel (hexane/acetone 25/1) to afford 7 as a colorless oil (2.396 g, 96%). 1H NMR spectra data were identical to those reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 14062-19-2, its application will become more common.

Reference:
Article; Kawasaki, Masashi; Kuroyanagi, Saki; Ito, Takuya; Morita, Hiroyuki; Tanaka, Yasuo; Toyooka, Naoki; Tetrahedron; vol. 73; 15; (2017); p. 2089 – 2099;,
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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. 14062-30-7, name is Ethyl 2-(3-bromophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl 2-(3-bromophenyl)acetate

5.2 g of the compound from the preceding step are dissolved in 70 ml of ethyl formate and, in small portions, 1.7 g of 60% NaH are added. Stirring is maintained at AT for 5 hours. The mixture is poured into 100 ml of 1N HCl and then extracted with AcOEt, and the extract is dried over MgSO4 and then evaporated to dryness. This gives 5.8 g of the expected compound in the form of an oil. NMR CDCl3 (300 MHz): 1.9 ppm: t: 3H; 4.20 ppm: q: 2H; 7.11-7.42 ppm: m: 5H; 12.06 ppm: d: 1H.

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 14062-30-7.

Reference:
Patent; sanofi-aventis; US2007/129365; (2007); 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. 541-16-2, name is Di-tert-Butyl malonate, A new synthetic method of this compound is introduced below., Recommanded Product: Di-tert-Butyl malonate

A solution of sodium hydride (0.040 g, 1.54 mmol) in THF (100mL) was cooled to 0C and treated with di-tert-butyl malonate (20.7 3 mL, 92.47 mmol) dropwise via dropping funnel, over 20 min. After stirring at room temperature for 30 min., 3,3-dimethylallyl bromide (9.7 mL, 83.22 mmol) was added. After stirring an additional 19 h, the reaction mixture was diluted with 10% HCl solution (100 mL) and EtOAc (100 mL). The resulting organic phase was washed with satd. aq. NaCl, dried over MgSO4, filtered, and concentrated to afford 25.74 g (94%)of a crude yellow oil. TLC: Rf 0.60 (silica, 10% ethyl acetate-hexane).

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; Bayer Corporation; EP923530; (2004); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 6942-39-8, name is Methyl 2-bromo-5-fluorobenzoate, A new synthetic method of this compound is introduced below., HPLC of Formula: C8H6BrFO2

A 500 mL round-bottom flask was charged with methyl 2-bromo-5- fluorobenzoate (48 g, 206 mmol), copper cyanide (37 g, 412 mmmol) and DMF (200 mL). The mixture was heated at 110 C overnight and then cooled to room temperature. Ether (1.5 L) and Celite (100 g) were added and the mixture was stirred at room temperature for 30 minutes. The solid was filtered and the filtrate was washed with brine (3 x 200 mL) and then dried over MgS04. The solvent was evaporated under reduced pressure to give the desired product as a colorless solid (31 g, 84%). MS : (ES) m/z calculated for C9H7FN02[M+H]+ 180.1, found 180.1.

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; CHEMOCENTRYX, INC.; CHEN, Xi; DRAGOLI, Dean, R.; FAN, Junfa; KALISIAK, Jaroslaw; KRASINSKI, Antoni; LELETI, Manmohan, Reddy; MALI, Venkat; MCMAHON, Jeffrey; SINGH, Rajinder; TANAKA, Hiroko; YANG, Ju; YU, Chao; ZHANG, Penglie; (198 pag.)WO2017/87607; (2017); A1;,
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Reference of 4934-99-0, 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. 4934-99-0 name is Methyl 3-hydroxycyclobutanecarboxylate, 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.

General procedure: To a flask containing alcohol (3 equiv.) in THF (0.1 – 0.5 M) at 0 C was added sodium hydride (3 equiv. 60% oil immersion). The resulting slurry was stirred 10 min and the alkyl bromide (1 equiv.) was added. The reaction mixture was allowed to reach rt and was stirred 2 h at which point NH4CI solution (saturated, 10 mL) was added followed by EtOAc (10 mL). The layers were separated, and the aqueous layer was extracted with EtOAc (3 x 10 mL). The combined organic layers were dried over anhydrous MgSOr, filtered and concentrated under reduced pressure and purified employing either silica gel flash chromatography (0-> I 00% EtO Ac/hexanes) or reverse-phase preparatory HPLC (Phenomenex Luna 10 m C18, 100A,150 x 30 mm, 5 ->95% MeCN (0.1% formic acid) in H2O, 25 min, 60 mL/min) to afford the desired product.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Methyl 3-hydroxycyclobutanecarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; DENALI THERAPEUTICS INC.; CRAIG, Robert A., II; DE VICENTE FIDALGO, Javier; ESTRADA, Anthony A.; FENG, Jianwen A.; FOX, Brian M.; LEXA, Katrina W.; OSIPOV, Maksim; SWEENEY, Zachary K.; THOTTUMKARA, Arun; (137 pag.)WO2019/183589; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics