Category: esters-buliding-blocks

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. 685-88-1, name is Diethyl fluoromalonate, A new synthetic method of this compound is introduced below., SDS of cas: 685-88-1

General procedure: All flasks and stirrer bars were flame dried before use. Tothe N-oxide (0.2 mmol, 1.0 equiv.), dissolved in 2 cm3dichloromethane was added Tf2O (0.3 mmol, 1.5 equiv.) at0 C. In another flask, a suspension of NaH (0.7 mmol, 3.5equiv.) in 1 cm3 tetrahydrofuran was cooled to 0 C andthe malonate (0.7 mmol, 3.5 equiv.) was added. After15 min, the malonate solution was added to the activatedN-oxide solution and the mixture was stirred at roomtemperature for 1 h. The reaction was quenched withNH4Cl solution and the aqueous phase was extracted withdichloromethane. The combined organic layers werewashed with brine before being dried over MgSO4. Thesolvents were removed under reduced pressure and thecrude product was purified by column chromatography.

The synthetic route of 685-88-1 has been constantly updated, and we look forward to future research findings.

Reference:
Erratum; Lemmerer, Miran; Teskey, Christopher J.; Kaiser, Daniel; Maulide, Nuno; Monatshefte fur Chemie; vol. 149; 4; (2018); p. 721 – 722;,
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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. 924-99-2, name is Ethyl 3-(dimethylamino)acrylate, A new synthetic method of this compound is introduced below., Application In Synthesis of Ethyl 3-(dimethylamino)acrylate

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 ¡Á 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. Ethyl-2-(2,5-difluoro-4-(pyrrolidin-1-yl)benzoyl)-3-(dimethylamino) acrylate (15)Yellow oil (Rf = 0.3), Yield 85%. IR (KBr) numax in cm-1:2993 (C-H, Ar), 2953 (C-H), 1760 (C=O), 1692 (C=O),1654 (C=C, Ar), 1592 (C-N). 1H NMR (400 MHz, DMSOd6):delta = 7.77 (1H, s, CH), 7.32 (1H, d, J = 5.0 Hz, CH-Ar),6.88 (1H, d, J = 5.2 Hz, CH-Ar), 4.2 (2H, q, J = 7.1 Hz,CH2), 3.47-3.42 (4H, m, 2CH2), 3.1 (6H, s, 2CH3), 2.01-1.97 (4H, m, 2CH2), 1.32 (3H, t, J = 4.2 Hz, CH3).

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

Reference:
Article; Almashal, Faeza A.; Alshawi, Jasim M.; Dhumad, Adil M.; Jassem, Ahmed M.; Medicinal Chemistry Research; (2020);,
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Reference of 685-88-1,Some common heterocyclic compound, 685-88-1, name is Diethyl fluoromalonate, molecular formula is C7H11FO4, 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.

Step 1: Synthesis of 2-( 1 -(2,3 -difluorobenzyl)-5 -(difluoromethoxy)- 1 H-pyrazol-3 -yl)-5- fluoropyrimidine-4,6-diol To a mixture containing diethyl 2-fluoromalonate (2 equiv.) and1 -(2,3 -difluorobenzyl)-5 -(difluoromethoxy)- 1 H-pyrazole-3 -carboximidamide hydrochloride (Described in step 3 towards the synthesis of Compound 1-52 (1 equiv.) in methanol was added a 25 wt% solution of sodium methoxide in methanol (5 equiv.). The mixture was stirred at 23 C for 1 h. To this mixture, was added HC1 (5 equiv.). The mixture was stirred vigorously for 15 mm. The precipitate formed was collected by filtration and dried under vacuum to deliver the desired intermediate, 2-( 1 -(2,3 -difluorobenzyl)-5-(difluoromethoxy)- 1 H-pyrazol-3 -yl)-5 -fluoropyrimidine-4,6-diol (475 mg, 44 % yield) as a cream colored solid.?H NMR (500 MHz, DMSO-d6) ppm 7.19 – 7.57 (m, 3 H), 7.11 – 7.16 (m, 1 H), 6.71 (s, 1 H), 5.41 (s, 2H).

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

Reference:
Patent; IRONWOOD PHARMACEUTICALS, INC.; RENHOWE, Paul Allen; SHEPPECK, James Edward; NAKAI, Takashi; IYER, Karthik; PERL, Nicholas Robert; RENNIE, Glen Robert; WO2015/89182; (2015); A1;,
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Electric Literature of 57486-68-7,Some common heterocyclic compound, 57486-68-7, name is Methyl 2-chlorophenylacetate, molecular formula is C9H9ClO2, 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.

Reference Example Al4; (1) To a solution of methyl 2-chlorophenylacetate (10 g) in dimethylformamide (150 mL) was added N, N- dimethylformamide dimethylacetal (14.4 mL) , and the mixture was stirred at 85C overnight. After cooling to room temperature, to the reaction mixture was added ethyl acetate and water. After stirring, the organic layer was separated, dried over sodium sulfate and filtered, and the filtrate was concentrated in vacuo. The residue was diluted with acetic acid (18 mL) , and -thereto were added 3- amino-4-ethoxycarbonyl-lH-pyrazole (8.4 g) and piperidine(1.1 mL) . The mixture was stirred at 800C for 3.5 hours.After cooling to room temperature, to the reaction mixture were added ethyl acetate and water. The mixture was stirred and filtered, and the resultant -? precipitates were dried to give 3- [2- (2-chlorophenyl) -2-methoxycarbonyl- vinylamino] -4-ethoxycarbonyl-lH-pyrazole (11.8 g, yield: 62%) as a powder. MS(APCI)m/z; 350/352 [M+H]+; Reference Example A14B; To a solution of methyl 2-chlorophenylacetate (25 g) in dimethylformamide (400 itiL) was added N, N- dimethylformamide diralphaethylacetal (36 itiL) , and the mixture was stirred at 90 C overnight. After cooling to room temperature, to the reaction mixture were added ethyl acetate and water. After stirring, the organic layer was separated, dried over magnesium sulfate and filtered, and the filtrate was concentrated in vacuo. The residue was diluted with acetic acid (60 itiL) , and thereto was added 3- amino~4-ethoxycarbonyl-5-methyl-lH-pyrazole (19.7 g) . The mixture was stirred at 1200C overnight. After cooling the reaction mixture to room temperature, the precipitates were collected by filtration, washed with ethyl acetate/diisopropylether (1/1) and dried to give 6- (2- chlorophenyl) -3-ethoxycarbonyl-2-methyl-7-oxo-4 , 7- dihydropyrazolo [1, 5-a] pyrimidine (26.0 g) as a powder. MS(APCI)m/z; 332/334 [M+H]+

The synthetic route of 57486-68-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; MITSUBISHI TANABE PHARMA CORPORATION; WO2008/4698; (2008); A2;,
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Application of 58656-98-7, 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. 58656-98-7, name is tert-Butyl 4-fluorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

Preparation of 4-[4-(2-Aminoethyl phenoxy]benzoic acid, tert-butyl ester Tyramine (700 mg, 5.1 mmol) was added to a magnetically stirred suspension of potassium hydride (35 wt. percent dispersion in oil; 876 mg, 7.64 mmol) in DMF (20 mL) at 25 C. After effervescence stopped, tert-butyl 4-fluorobenzoate (1.0 g, 5.1 mmol) was added. After stirring at 25 C. for 64 hours, the reaction was warmed to 60 C. After 48 h, the reaction was poured into brine and extracted with hexanes (3*25 mL) and ethyl acetate (2*25 mL). Organic layers washed separately with aqueous 2 N NaOH, dried (Na2SO4), then pooled, evaporated and purified by silica gel chromatography (CH2Cl2:MeOH/2:1) to provide 0.98 g of clear oil.

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

Reference:
Patent; Brewster, William Kirkland; Demeter, David Anthony; Erickson, William Randal; Klittich, Carla Jean Rasmussen; Lowe, Christian Thomas; Rieder, Brent Jeffrey; Nugent, Jaime Susanne; Yerkes, Carla Nanette; Zhu, Yuanming; Balko, Terry William; US2007/93498; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 140-39-6, name is p-Tolyl 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 140-39-6, HPLC of Formula: C9H10O2

General procedure: Catalyst (FSG) was purchased from Fluorous Technologies Inc. and used without further purification. Its synthesis procedure is reported by Curran et al. [24]. General procedure for Fries rearrangement was done by adding FSG to aryl ester at the ambient temperatures. Before adding FSG to reaction mixture, aryl esters were obtained by in situ formation through the reaction of acyl chloride derivatives and phenol derivatives. Thus, to a 100ml round bottom flask stirring by a magnetic bar 10mmol of phenols was added and then, 10mmol of acyl chloride derivatives (for catechols 20mmol) was added dropwise and allowed to react at room temperature. After 30min, temperature was raised to remove HCl from reaction mixture. Then 1g of FSG was added to reaction mixture at ambient temperature. After 4h heating at appropriate temperature in oil bath, the reaction mixture was cooled to room temperature and washed with dichloromethane. The catalyst was separated by filtration. The solvent was removed by rotary evaporator and resulting mixture was separated by column chromatography (stationary phase: silica-gel, eluent:hexane:ethyl acetate) and purified by recrystallization. All isolated products successfully gave related spectral data of IR, NMR, and mass spectrometers.

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; Ghaffarzadeh, Mohammad; Ahmadi, Maryam; Journal of Fluorine Chemistry; vol. 160; (2014); p. 77 – 81;,
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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. 2318-25-4, name is Ethyl 3-ethoxy-3-iminopropionate hydrochloride belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. SDS of cas: 2318-25-4

Example P2: Preparation of Ethoxycarbonimidoyl-acetic acid ethyl ester. 25.7 g (0.131 mol) of ethoxycarbonimidoyl-acetic acid ethyl ester hydrochloride was suspended in 155 ml of dichlormethane and then a solution of 5.78 g (0.144 mol) of sodium hydroxide in 30 ml of water was added. After stirring for 30 min the layers were separated and the organics dried and vacced down to leave a colourless oil to give 19.35g of clean Ethoxycarbonimidoyl-acetic acid ethyl ester. 1H-NMR (CDCI3, ppm): 6.28 (s, br, 1 H), 4.19 (q, J=7 Hz, 2H), 4.02 (m, 2H), 3.37 (s, 1 H), 3.25 (s, 1 H), 1.30 (t, J=7Hz, 3H), 1.26 (t, J=7Hz, 3H).

The synthetic route of 2318-25-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; SYNGENTA PARTICIPATIONS AG; SYNGENTA LIMITED; WO2008/6540; (2008); 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 56741-34-5 as follows. HPLC of Formula: C8H8FNO2

[00326] To a stirred solution of methyl 5-amino-2-fluorobenzoate (500 mg, 2.99 mmol) in DCM (20 mL) at 0 C, was added 3,4-difluorobenzoyl chloride (410 mu, 3.26 mmol) followed by TEA (1.0 mL, 7.48 mmol). The mixture was allowed to warm to rt and stirred for 72 h. The mixture was diluted with water and the organic layer separated and concentrated under reduced pressure. The obtained solid was purified via trituration with Et20 to afford compound 1 (782 mg, 84%) as a white solid. 1H MR (400 MHz, DMSO-i): delta 10.53 (s, 1H), 8.35 (m, 1H), 8.00 – 8.10 (m, 2H), 7.88 (m, 1H), 7.66 (m, 1H), 7.38 (m, 1H), 3.85 (s, 3H); LCMS Mass: 310.0 (M++l).

According to the analysis of related databases, 56741-34-5, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SIDECAR THERAPEUTICS, INC.; ROWBOTTOM, Martin W.; (183 pag.)WO2018/183122; (2018); A1;,
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Electric Literature of 57486-68-7, 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. 57486-68-7, name is Methyl 2-chlorophenylacetate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dark red solution of (2-chlorophenyl)acetic acid methyl ester (TCI, 1.53 mL, 10.0 mmol), NIS (2.36 g, 10.5 mmol) and AuCl3 (152 mg, 0.50 mmol) in DCE (25 mL) was stirred at reflux under Ar for 18 h. The solution was cooled to RT, NIS (563 mg, 2.50 mmol) added and the purple solution stirred at reflux for 2 h. The solution was cooled to RT, filtered through Celite and the filtercake washed with DCM. The combined organics were concentrated in vacuo to leave a solid that was dissolved in diethyl ether (50 mL), washed with water (2 x 50 mL), brine (50 mL), dried (Na2S04), filtered and concentrated in vacuo to leave a purple oil (3.0 g). FCC, using 2-7% EtOAc in cyclohexane, gave the title compound as a clear oil (1.07 g, 34%) and a clear oil (mixed fractions, 814 mg, 26%). LCMS (Method 3): Rt 4.09 min, m/z 311 [MH+].

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

Reference:
Patent; CHIESI FARMACEUTICI S.P.A.; ALCARAZ, Lilian; HURLEY, Christopher; CRIDLAND, Andrew, Peter; JENNINGS, Andrew, Stephen, Robert; WO2014/195402; (2014); 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. 35418-07-6, name is Methyl 3-(4-aminophenyl)propanoate, This compound has unique chemical properties. The synthetic route is as follows., Recommanded Product: 35418-07-6

Methyl 4-[N,N-bis(2-hydroxyethyl)amino]phenylpropionate Methyl 3-(4-aminophenyl)propionate (4.3 g; 24 mmol) was reacted with 11 g (250 mmol, 10 equivalents) of ethylene oxide in 24 ml of 30% acetic acid in a similar manner to Reaction 3 in Example 21. The reaction mixture was worked up. The crude product so obtained was purified by chromatography on a silica gel column (methylene chloride/2-4% methanol) and then crystallized from n-hexane-ethyl ether, whereby 5.04 g (18.9 mmol) of the title compound were obtained as white crystals (yield: 78.6%).

According to the analysis of related databases, 35418-07-6, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Mitsui Chemicals, Inc.; US5852011; (1998); A;,
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