Tag: M.W=100-200

Application of 4630-80-2, 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 4630-80-2 as follows.

To a suspension of NaH (2.75 g, 68.7 mmol) in THF (15 ml_) at 700C was added dropwise a solution of methyl cyclopentanecarboxylate (8.00 g, 62.4 mmol) and anhydrous acetonitrile (3.91 ml_, 74.9 mmol) in THF (5 ml_). The mixture was stirred for 16 h at 70C-72C, cooled to rt, and diluted with ethyl acetate and aqueous HCI. The organic layer was washed successively with water and brine and dried (MgSO4), filtered and concentrated under reduced pressure to provide the title compound, which was used without further purification.

According to the analysis of related databases, 4630-80-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BAYER PHARMACEUTICALS CORPORATION; WO2007/64872; (2007); A2;,
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Reference of 2905-65-9, 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. 2905-65-9, name is Methyl 3-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

NaHMDS (2M, 5.50 mL) was added to a solution of pent-4-enenitrile (0.97 mL, 10.0 mmol) in anhydrous THF (50 mL) at -78 oC. After stirring for 15 min, methyl-3-chlorobenzoate (1.88 g) was added and the reaction was stirred for 30 min befor warming to room temperature. The reaction was quenched by addition of 1N HCl solution, then extracted with EtOAc (x 2). The combined organics were dried and concentrated to give the acylated nitrile (2.18 g, 99%). Hydroxylamine hydrochloride (382 mg) was added to a solution of the acylated nitrile (1.1 g) in pyridine (10 mL) and the reaction was stirred at 80 oC for 3 hours. After cooling to room temperature, EtOAc and sat. NH4Cl solution were added and the layers separated. The organic was washed with brine, dried over Na2SO4 and concentrated to give the amino-isoxazole as a yellow oil (1.05 g, 89%) which was used directly. The residue was dissolved in pyridine (5 mL) and cooled in an ice-bath. AcCl (0.36 g, 4.5 mmol) was added and the reaction was stirred for 30 min before warming to room temperature for a further 30 min. The volatiles were removed under vacuum and the residue was purified by silica gel chromatography [heptane/EtOAc, 9:1 – 3:1] to give the product as a colourless oil (0.96 g, 77%). The N-acyl intermediate (950 mg, 3.43 mmol) was then N-alkylated with allyl bromide and NaH to give the product 19 as a colourless oil (855 mg, 79%)

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

Reference:
Article; Moss, Thomas A.; Tetrahedron Letters; vol. 54; 8; (2013); p. 993 – 997;,
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Related Products of 140-39-6, The chemical industry reduces the impact on the environment during synthesis 140-39-6, name is p-Tolyl Acetate, I believe this compound will play a more active role in future production and life.

General procedure: A mixture of aryl ester (25 mmol), HFSiO2 (2 g), and EtOAc (5 mL) was charged in a 50 ml flask and stirred for 5min. EtOAc was used for homogenization of the reactionmixture in this step. The solvent was evaporated under vacuumand the residue was heated with the classical method for 4 h at 55C for aryl acetates and at 75C for aryl benzoates(Table 1). After cooling, the reaction mixture was extractedwith EtOAc (3 × 10 mL) and the solvent was removed under vacuum. The residue was subjected to short column chromatography (EtOAc/hexane; 1:5) on silica gel to obtain pureproducts. All the isolated hydroxyaryl ketones successfullygave the related spectral data of IR, 1H NMR, 13C NMR andMS spectrometers (see the Supporting Information, Fig. 12S-39S) and comparison with authentic samples prepared byreported methods [33-36].

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, p-Tolyl Acetate, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Paghandeh, Hossein; Saeidian, Hamid; Ghaffarzadeh, Mohammad; Letters in Organic Chemistry; vol. 15; 9; (2018); p. 809 – 814;,
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Reference of 681128-38-1,Some common heterocyclic compound, 681128-38-1, name is Ethyl 3,3-difluorocyclobutanecarboxylate, molecular formula is C7H10F2O2, 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 the compound described in Preparation 42 (2.30 g, 14 mmol), in diethyl ether (14 ml_), was added to a suspension of lithium aluminium hydride (1.17 g, 30.8 mmol), in diethyl ether (70 ml_), cooled to -45 0C. This mixture was stirred at -45 0C for 1 hour, then warmed to -10 0C for 1 hour. It was then slowly warmed to room temperature and stirred for 15 hours, After which time it was cooled to 4 0C and quenched with sequential addition of water (1.2 ml_), 10% aqueous solution of sodium hydroxide (1.2 ml_) and finally water (3.6 ml_). Diethyl ether (50 ml_) was then added and the solution was allowed to stir for 90 minutes. The organic layer was separated and the aqueous phase was back extracted with diethyl ether (3 x 50 ml_). The combined organic layers were dried over magnesium sulphate, filtered, and concentrated under reduced pressure to give a 45% solution of the title compound in diethyl ether (1.56 g, 92%). 1H-NMR (400 MHz, CDCI3): delta 2.30 (m, 3H), 2.60 (m, 2H), 3.65 (m, 2H).

The synthetic route of 681128-38-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; PFIZER LIMITED; GIBSON, Karl Richard; GREEN, Martin Peter; UNDERWOOD, Toby James; WAKENHUT, Florian; WO2010/32200; (2010); 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 816-27-3 as follows. SDS of cas: 816-27-3

To a solution of 1-amino-5-(1,1-difluoropropyl)pyrrolidin-2-one (120 mg, 0.67 mmol) in ethanol (5 mL) was added ethyl 2-ethoxy-2-imino-acetate (489 mg, 3.37 mmol). The reaction mixture was stirred at 60 C. for 16 h and subsequently concentrated under reduced pressure to afford ethyl 2-[[2-(1,1-difluoropropyl)-5-oxo-pyrrolidin-1-yl]amino]-2-imino-acetate (600 mg, 80%, 40% purity) as a yellow oil, used as is in the next step.

According to the analysis of related databases, 816-27-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Genentech, Inc.; Patel, Snahel; Hamilton, Gregory; (73 pag.)US2018/170927; (2018); A1;,
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Electric Literature of 106-65-0, A common heterocyclic compound, 106-65-0, name is Dimethyl succinate, molecular formula is C6H10O4, 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 11 Methyl alpha-formylsuccinate In a modification of the procedure of Fissekis and Sweet, Biochemistry 1970, 9, 3136-42, sodium methoxide (40.5 g, 0.75 mol) was suspended in dry ether (500 mL) and stirred under nitrogen at 0 C. A mixture of dimethylsuccinate (65.4 mL, 0.50 mol) and methylformate (123 mL, 2.00 mol) was added dropwise over 30 minutes. The reaction mixture was stirred at 0 C. for 2 hours and then at room temperature overnight. Subsequently, the reaction mixture was evaporated to a viscous brown residue which was washed once with petroleum ether and then dissolved in 3 M hydrochloric acid (160 mL). This solution was made weakly acidic with concentrated hydrochloric acid and then extracted with dichloromethane (4*250 mL). The organic phase was dried (MgSO4), filtered and evaporated under reduced pressure. The resulting residue was distilled in a kugelrohr apparatus at 60 C. and 0.6 mBar yielding 52.3 g of a mixture of the title compound and dimethyl succinate in the molar ratio 80:20 (determined by NMR) as a colorless oil. This mixture can be used directly in the following preparation. The product can be isolated free of dimethyl succinate by exchanging the extraction with dichloromethane with a continuous extraction with diethyl ether. However, in our hands this reduced the yield to 34%. Fissekis and Sweet,ibid, had reported a 62% yield. 1H-NMR (DMSO-d6/TMS): delta=3.20 (s, 2H, CH2); 3.59 (s, 3H, OMe); 3.61 (s, 3H, OMe); 7.73 (s, 1H, CHOH); 10.86 (br s, 1H, CHOH). 13C-NMR (DMSO-d6/TMS): delta=28.9 (CH2); 51.0 (OMe); 51.6 (OMe); 102.1 (C=CHOH); 156.6 (CHOH); 168.3 (COO); 171.7 (COO).

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; Nielsen, Peter E.; US6300318; (2001); B1;,
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Related Products of 7364-20-7, These common heterocyclic compound, 7364-20-7, name is Methyl 4-ethylbenzoate, 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.

General procedure: (Diacetoxyiodo)benzene (5 mmol, 1.61 g), I2 (0.4 mmol, 102 mg), p-toluenesulfonamide (0.4 mmol, 68.4 mg), and ethylbenzene (2 mmol, 184 mg) were added to dichloroethane (3 mL). The mixture was warmed at 60 C for 2 h under an argon atmosphere. Then, the mixture was poured into saturated aqueous sodium sulfite solution and extracted with diethyl ether (3 × 20 mL). The organic layer was dried over Na2SO4. After filtration and removal of the solvent under reduced pressure, the residue was subjected to preparative TLC on silica gel using a mixture of hexane and ethyl acetate (5:1) as an eluent to give alpha-(acetoxy)ethylbenzene in 63% yield.

Statistics shows that Methyl 4-ethylbenzoate is playing an increasingly important role. we look forward to future research findings about 7364-20-7.

Reference:
Article; Baba, Haruka; Moriyama, Katsuhiko; Togo, Hideo; Tetrahedron Letters; vol. 52; 33; (2011); p. 4303 – 4307;,
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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. 37746-78-4, name is (E)-Ethyl 4-bromobut-2-enoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. name: (E)-Ethyl 4-bromobut-2-enoate

General procedure: To a vigorously stirring solution of alpha-imino ester 1 (0.5 mmol,1 equiv) and E-ethyl-4-bromocrotonate or methyl-4-bromocrotonate (2, 1.5 mmol, 3 equiv) in EtOH (2 mL) was added indium powder (1 mmol, 2 equiv). The mixture was allowed to stir vigorously for 6 h at 30 C. After this period, the reaction mixturewas quenched with 2 mL of water and transferred to a separating funnel and extracted using ethyl acetate (315 mL). The combined organic layers were dried over anhydrous Na2SO4. Then the solvent was evaporated under vacuum. Purification of the resulting crude reaction mixture by column chromatography on silica gel (EtOAc/Hexane as eluent) gave the product 3 (see Tables 1 and 2 and Scheme 2 for individual entries).

The synthetic route of 37746-78-4 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Aslam, Nayyar Ahmad; Babu, Srinivasarao Arulananda; Sudha, Arya Jayadev; Yasuda, Makoto; Baba, Akio; Tetrahedron; vol. 69; 32; (2013); p. 6598 – 6611;,
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Adding a certain compound to certain chemical reactions, such as: 5335-05-7, name is Chloromethyl benzoate, 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 5335-05-7, Safety of Chloromethyl benzoate

To a stirred mixture of with NaH (60%, 50 mg, 1.3 mmole) in anhydrous DMF (6 mL) at room temperature under nitrogen was added 2-(6-(4-(2-(tert-butyl-dimethylsilyloxy)ethyl)piperazin-1-yl)-2-methylpyrimidin-4-ylamino)-N-(2-chloro-6-methylphenyl)thiazole-5-carboxamide, 10 (0.20 g, 0.34 mmole). The resultant mixture was stirred at room temperature for 8 min., then treated with chloromethyl benzoate (0.2 g, 1.2 mmole), the reaction mixture was stirred at room temperature overnight. The reaction mixture was added with aqueous NH4Cl solution and extracted with EtOAc (3×45 mL). The EtOAc solution was washed with 10% LiCl solution and concentrated to an oily residue. The residue was purified by prep. HPLC to give a white solid as impure product and used directly in next step. MS (ESI, M+H+) 736, 738.

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; Kim, Kyoung S.; Lee, Francis Y.; Lombardo, Louis J.; Luo, Feng Roger; Wityak, John; US2006/69101; (2006); A1;,
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Some common heterocyclic compound, 27798-60-3, name is Methyl 2-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. name: Methyl 2-Methoxyphenylacetate

Triflic acid (7.3 mL, 43.4 mmol) was added dropwise to a solution of thioxanthone oxide (5.00 g, 21.7 mmol) and methyl 2-(2-methoxyphenyl)acetate (4.31 g, 23.9 mmol) in DCM (60 mL) at -78 C. and slowly warmed to 25 C. overnight. The reaction mixture was quenched with water (100 mL), the layers separated, and the aqueous phase washed with water (4×100 mL) and concentrated to a crude solid. The crude solid was dissolved in minimal acetone, precipitated into MTBE (1 L), and filtered to afford the title compound (10.0 g, 85%) as a white solid. 1H NMR (500 MHz, (CD3)2CO) delta: 8.66-8.69 (m, 2H), 8.19-8.22 (m, 3H), 8.10-8.13 (m, 4H), 7.91 (d, J=2.5 Hz, 1H), 7.37 (d, J=9 Hz, 1H), 3.96 (s, 3H), 3.61 (s, 2H), 3.57 (s, 3H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 27798-60-3, its application will become more common.

Reference:
Patent; Rohm and Haas Electronic Materials, LLC; LaBeaume, Paul J.; (24 pag.)US9304394; (2016); B2;,
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