Category: esters-buliding-blocks

25542-62-5, A common compound: 25542-62-5, name is Ethyl 6-bromohexanoate, 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.

Example 9 Synthesis of 3-[3-(5-carboxypentyl)-5-iodo-2,3-dimethyl-3H-1-indoliumyl]-1-propanesulfonate (2) A mixture of 13.4 g (0.12 mol) of potassium tert-butoxide and 100 g of tert-butanol was stirred and heated until the tert-butoxide totally dissolved. The solution was cooled to about 50 C. and 17 g (0.12 mmol) of ethyl 2-methylacetoacetate was added dropwise. Ethyl-6-bromohexanoate (30 g, 0.13 mmol) was then added dropwise and the reaction mixture was stirred and refluxed for 5 hours. The mixture was filtered and the solvent was removed under reduced pressure. The residue was partitioned between 1M HCl and chloroform. The organic layer was dried over magnesium sulfate and purified on silica gel using 1:10 ethyl acetate/hexane as the eluent to yield 25 g (75%) of diethyl 2-acetyl-2-methyloctanedioate (3) as yellow liquid.

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, Ethyl 6-bromohexanoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; NANOQUANTUM SCIENCES, INC.; Jones, Gary W.; Tatarets, Anatoliy L.; Patsenker, Leonid D.; US2013/231604; (2013); A1;,
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344-14-9,Some common heterocyclic compound, 344-14-9, name is Dimethyl 2-fluoromalonate, molecular formula is C5H7FO4, 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.

To a stirred solution of dimethyl fluoromalonate (1 mmol, 150.11 mg) in anhydrous methanol (10 ml) was added a solution of n-octylamine (1 mmol, 166 mul) in methanol (5 ml) drop wise over the period of one hour at room temperature. It was then further stirred at room temperature for two hours. The solution was rotary evaporated and the residue redissolved in ethyl acetate. The ethyl acetate solution was sequentially washed with 2 M HCI (2×10 ml) and saturated sodium chloride (1×15 ml) solution. Drying over MgSO4 and rotary evaporation of organic solvent gave white solid that was a mixture of bisamide and ethyl 4-aza-2-fluoro-3-oxododecanoate. Desired product was purified as a white solid by PLC in 40-60 petroleum ether – diethyl ether (3:2), (117 mg, 47%).TLC Rf 0.23, petroleum ether- diethyl ether (3:2)1H NMR (400 MHz, CDCI3) delta 0.88 (3H, t, J 6.4 Hz, (CH3(CH2)/), 1.29 (10H, m, CH3(CH2)5), 1.54 (2H, br s, CH3(CH2)5CH2), 3.32 (2H, m, J 6.6 Hz, CH3(CH2)6CH2), 3.9 (3H, s, OCH3), 5.28 (1 H, d, J 49.2, C(H)F), 6.42 (1 H, s, NH).

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

Reference:
Patent; THE UNIVERSITY OF NOTTINGHAM; WO2007/135466; (2007); A2;,
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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. 18448-47-0, name is Methyl cyclohex-1-enecarboxylate, A new synthetic method of this compound is introduced below., 18448-47-0

(4) Take 3.9g of 0.8g potassium carbonate (K2CO3),0.6g palladium on carbon (Pd (OH) 2 / C) and23mL tert-butyl hydroperoxide (TBHP),0 C was sequentially added to 80 mL of dichloromethane (DCM),The temperature was naturally raised to room temperature until the reaction was completed, and the allyl site was oxidized to form a carbonyl group.The reaction solution was then extracted with DCM, and the extract was separated by silica gel column chromatography.It is obtained that when R = H,4.1 g of product were obtained; when R = CH3,4.15 g of product was obtained.The reaction yield was 85%.

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; Shenzhen Elderly Medical Institute; Wu Zhengzhi; Tao Cheng; Liu Jieren; Li Limin; (6 pag.)CN110229064; (2019); A;,
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4224-69-5, 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 4224-69-5 as follows.

General procedure: To a solution of 2a (0.30 g, 0.89 mmol) in a mixture of THF: H2O (20 mL, 2:1, v/v) were added allyl bromide (0.161 mL, 1.33 mmol) and indium powder (0.153 g, 1.33 mmol) and the reaction was continued for 3 h. On completion as monitored by TLC, the excess solvent was removed from the reaction to obtain a residue which was extracted with EtOAc (40 mL) and water (30 mL). The water layer was separated and further extracted with EtOAc (2 x 20 mL) and the organic layers were pooled, dried over anhyd. Na2SO4, and evaporated in vacuum to afford 3d (0.318 g, 93%) which was used further without purification.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, 4224-69-5, and friends who are interested can also refer to it.

Reference:
Article; Yadav, Veena D.; Srivastava, Kumkum; Tripathi, Renu; Batra, Sanjay; Tetrahedron; vol. 73; 38; (2017); p. 5680 – 5689;,
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581065-95-4, 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 581065-95-4 as follows.

The preparation of compound D is disclosed in Cheng et al. 2013 (compound 108, FIG. 19). The preparation of compound E is disclosed in Cong et al. 2015 (compound 21, FIG. 2b). Compound F was prepared from tert-butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate (CAS Reg. No. 581065-95-4) by treatment with Fmoc-Cl to attach the Fmoc protecting group, followed by treatment with trifluoroacetic acid to cleave the t-butyl ester.

According to the analysis of related databases, tert-Butyl 1-amino-3,6,9,12-tetraoxapentadecan-15-oate, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; Young, Ian S.; Lou, Sha; Gangwar, Sanjeev; (16 pag.)US2019/388553; (2019); A1;,
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Ester – an overview | ScienceDirect Topics

Adding some certain compound to certain chemical reactions, such as: 18013-97-3, name is Diethyl 2,5-dibromoterephthalate, 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 18013-97-3. 18013-97-3

To the crude was added anhydrous Lambda/,/V-dimethylformamide (100 cm3), 2,5-dibromo-terephthalic acid diethyl ester (1 1 .0 g, 29 mmol) and bis(triphenylphosphine)palladium(ll) dichloride (612 mg, 0.87 mmol) and the mixture heated at 100 C for 2 hours. The mixture allowed to cool to 23 C, concentrated in vacuo and passed through a plug of silica (dichloromethane) to give a solid which was triturated in methanol. The solid collected by filtration to give 2,5-bis-thieno[2,3-b]thiophen-2-yl- terephthalic acid diethyl ester (1 1 .68 g, 81 %) as a yellow solid. 1H-NMR (400 MHz, CDCIs) 1 .13 (6H, t, J 7.1 ), 4.24 (4H, q, J 7.1 ), 7.24 (2H, d, J 5.2), 7.26 (2H, s), 7.37 (2H, d, J 5.2), 7.88 (2H, s).

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 Diethyl 2,5-dibromoterephthalate.

Reference:
Patent; MERCK PATENT GMBH; MORSE, Graham; HEARD, Kane; MITCHELL, William; KROMPIEC, Michal; D’LAVARI, Mansoor; PRON, Agnieszka; (260 pag.)WO2019/52935; (2019); A1;,
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139102-34-4, 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. 139102-34-4, name is Methyl 4-bromo-2-methoxybenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

L1BH4 (0.66 g) was added portion- wise to a solution of methyl 4-bromo-2- methoxybenzoate (5 g) in dry THF (50 mL) and EtOH (10 mL) was added. The reaction was stirred for 18h. The mixture was then poured into aq. NaOH (1M, 300 mL) and extracted with EtOAc. The organics were combined, washed with water then sat. brine before being dried (MgS04), and concentrated in vacuo to give the sub-title compound (4.4 g) as a gum; 1H NMR: 7.30 (d, 1H), 7.17-7.11 (m, 2H), 5.10 (t, 1H), 4.43 (d, 2H), 3.79 (s, 3H).

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

Reference:
Patent; ASTRAZENECA AB; DAINIPPON SUMITOMO PHARMA CO., LTD.; ASTRAZENECA UK LIMITED; BAILEY, Andrew; HIGHTON, Adrian John; MCINALLY, Thomas; MOCHEL, Tobias; URABE, Daisuke; WO2012/66335; (2012); A1;,
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57486-68-7, 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. 57486-68-7, name is Methyl 2-chlorophenylacetate, A new synthetic method of this compound is introduced below.

General procedure: To a solution of dry diisopropylamine (0.3 mL, 2.17 mmol) in dry THF (3 mL) in two-necked flask was added n-butyllithium (2.5M solution in hexane, 0.87 mL, 2.17 mmol) at -78 to 0 for 1 h, and recooled to -78 , the acetic ester (6a-f, 200 mg, 1.083 mmol) dissolved in dry THF (6.4 mL) was added by a syringe within 30 min. The mixture was stirred at -78 for 30 min, and subsequently the 4a-d (260 mg, 1.192 mmol) dissolved in dry THF (2.6 mL) was added by syringe. The mixture was vigorously stirred for 3 h. The reaction mixture was quenched by ammonium chloride aqueous solution and the mixture was extracted with ethyl acetate, the organic layer was dried over sodium sulfate, filtered and concentrated reduced pressure. The residue was purified by flash column chromatography (SiO2, EA/Hex=1/10) to give 7a-v.

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; Park, Jung-Eun; Song, Chiman; Choi, Keehyun; Sim, Taebo; Moon, Bongjin; Roh, Eun Joo; Bioorganic and Medicinal Chemistry Letters; vol. 23; 20; (2013); p. 5515 – 5518;,
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18595-18-1, A common compound: 18595-18-1, name is Methyl 3-amino-4-methylbenzoate, 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.

The requisite 4-methyl-3-(pyridine-4-carbonylarnino)benzoic acid starting material (Step3) was prepared as follows: Step 1: Preparation of methyl 4-methyl-3-(pyridine-4-carbonylamino)benzoate; A solution of methyl 3-amino-4-methyl-benzoate (8.255 g, 50 mmol) and TEA (13.9 mL, 100 mmol, 2 eq) in DCM (200 mL) was cooled in an ice-bath and pyridine-4-carbonyl chloride (9.795 g, 55 mmol, 1.1 eq) was added portionwise as a solid. The reaction mixture was stirred for 30 mins, the ice-bath was removed, and stirring continued for a further 1 hr. Extra acid chloride (2 g, 0.2 eq) was added and the reaction mixture stirred a further 1 hr. It o was then diluted with more DCM and the resulting solution washed sequentially with water (twice), saturated sodium bicarbonate solution, and brine. At this stage a solid started to precipitate out, so more DCM was added. The solid precipitate (2 g) was isolated by titration and the filtrate dried (PS Paper) and evaporated to give a solid (10.7 g). The two fractions were identical (NMR, LCMS) and combined to give the title compound (12.7 g) 5 as a yellow solid, 1H NMR (400.132 MHz, DMSO) 62.33 (s, 3H),3.86 (s, 3H),7.46 (d, 1H),7.79 (d, 1H),7.87 -7.94 (m, 2H),7.98 – 8.05 (m, 1H),8.81 (d, 2H),10.35 (s, IH), m/z 271 (M+H+) 269 (M-H”).

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-amino-4-methylbenzoate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; ASTRAZENECA AB; ASTRAZENECA UK LIMITED; WO2008/59214; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 94-60-0 name is Dimethyl cyclohexane-1,4-dicarboxylate, 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. 94-60-0

Comparative Examples 1-3Using the same procedure as in Examples 7-9, DMCD was hydrogenated using a commercially available copper chromite catalyst. Analysis of the reactor effluent was carried out by gas chromatography and the results are shown in Table 3 as area %. TABLE 3 DMCD Hydrogenation Using Copper Chromite Catalyst Press: 345 barg Feed Rate: 1500 mL/hour Catalyst: CuCr Comp. Temp Mono- trans cis % cis/trans Example ( C.) DMCD ester CHDM CHDM MeOH Water Imp. Conv Ratio 1 205 19.3 11.2 17.6 20.3 31.0 0.3 0.3 77.4 1.2 2 215 16.4 10.6 24.2 23.0 25.8 0.1 0.1 82.6 1.0 3 225 8.3 6.3 26.7 21.3 36.8 0.3 0.2 90.0 0.8

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Dimethyl cyclohexane-1,4-dicarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Eastman Chemical Company; US6919489; (2005); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics