Author: Jessica.F

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. 75567-84-9, name is Methyl 3-(4-bromophenyl)propanoate, A new synthetic method of this compound is introduced below., SDS of cas: 75567-84-9

General procedure: Methyl 3-(4-bromophenyl)propanoate31 1 (1.0 equiv) and the appropriate commercially available (substituted-phenyl)boronic acid (1.5 equiv) were dissolved in a mixture of dioxane/EtOH (1:1) (concentration 1 mL/mmol) and 1 M aqueous NaHCO3 (2.0 equiv). To the solution, Pd(PPh3)4 (2.5 mol %) was added and the mixture was heated in the microwave at 100 C for 3 h, after which TLC showed full conversion. The reaction mixture was concentrated in vacuo, acidified to pH = 1 using 1 M HCl (aq), extracted with EtOAc, dried over MgSO4 and concentrated under reduced pressure. Purification by column chromatography eluting with CH2Cl2/Pet. ether (2:1) yielded the desired biphenyl esters as solids.

The synthetic route of 75567-84-9 has been constantly updated, and we look forward to future research findings.

Reference:
Article; Van Veldhoven, Jacobus P.D.; Liu, Rongfang; Thee, Stephanie A.; Wouters, Yessica; Verhoork, Sanne J.M.; Mooiman, Christiaan; Louvel, Julien; Ijzerman, Adriaan P.; Bioorganic and Medicinal Chemistry; vol. 23; 14; (2015); p. 4013 – 4025;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

A common compound: 1731-86-8, name is Methyl undecanoate, 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. 1731-86-8

General procedure: The synthesis of the AKGs was performed following the literature with some modifications (Baumann and Mangold 1964; Hanus et al. 2001; Appendino et al. 2003; Parkkari et al. 2006). LiAlH4 (550 mg, 14.5 mmol) was added slowly to a solution of the corresponding methyl ester (3.4 mmol) in anhydrous tetrahydrofuran (15 mL) at 0C and stirred for 1 h and was then left at 20C for 20 h. The reaction mixture was washed with NaOH (10%) followed by HCl (10%) and extracted with diethyl ether (3 × 20 mL); the extract was neutralized with saturated NaHCO3, dried under reduced pressure and purified by CC. The alcohol obtained was subsequently mesylated in absolute pyridine (4.5 mL, 55.6 mmol) at 0C by the addition of MsCl (880 mg, 7.65 mmol) and the solution was maintained for 24 h at 20C. After quenching the reaction with 5 mL of degasified water, the solution was extracted with diethyl ether (4 × 20 mL). The organic phase was washed with H2SO4 (2 N), neutralized, concentrated in vacuo, and the crude mesylate was purified by CC. KOH (127 mg, 2.26 mmol) was added to the chiral precursor (R)-solketal (283 mg, 2.14 mmol) in anhydrous toluene (2 mL). The reaction stirred at 50C for 1 h before the addition of metallic Na (3 mg, 0.15 mmol) followed by the mesylate dissolved in toluene (15 mL), and the resulting mixture was kept at 50C for 72 h. The reaction was quenched with HCl (10%) and extracted with ethyl ether (4 × 20 mL). The organic phase was neutralized, concentrated and purified by CC to give 1-O-alkyl-2,3-O-isopropylidene-sn-glycerol. This intermediate was deprotected in 5 mL of HCl:MeOH (1:10 v/v) and refluxed overnight. After the addition of H2O (10 mL) and extraction with diethyl ether (4 × 20 mL), the organic phase was neutralized, evaporatedto dryness in vacuo, and the residue was purified by CC to afford pure AKGs. Each step in the synthesis was monitored by TLC, and all CC steps were eluted with hexane-toluene-ethyl acetate (10:0:0-0:10:0-0:0:10) mixtures. The structures of the synthesised compounds were confirmed by 1H, 13C APT NMR with COSY, HMQC, HMBC and ESI-MS or HRESI-MS spectra along with the specific optical rotation.

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, 1731-86-8, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Fernandez Montoya, Deicy J.; Contreras Jordan, Luis A.; Moreno-Murillo, Barbara; Silva-Gomez, Edelberto; Mayorga-Wandurraga, Humberto; Natural Product Research; (2019);,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

7270-63-5, name is 5-Diazo-2,2-dimethyl-1,3-dioxane-4,6-dione, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: 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. 4.2.13. 2,4-Bis(4-(trifluoromethyl)phenyl)-6H-furo[2,3-b]pyran-6-one (5l). Reaction of 1 (85 mg, 0.5 mmol) and 4-ethynyl-alpha,alpha,alpha-trifluorotoluene (187 mg, 1.1 mmol) under Rh2(OPiv)4 (6 mg, 0.01 mmol) afforded 5l (106 mg, 50%) as a solid: mp 158-160 C; 1H NMR (300 MHz, CDCl3) delta 7.82 (2H, d, J=8.1 Hz), 7.76-7.73 (4H, m), 7.65 (2H, d, J=8.1 Hz), 6.94 (1H, s), 6.26 (1H, s); 13C NMR (75 MHz, CDCl3) delta 158.6, 152.1, 147.3, 138.4, 131.9, 128.2, 127.9, 126.4, 126.3, 126.3, 126.1, 126.0, 125.1, 123.7, 106.4, 102.4, 99.5; IR (KBr) 3125, 1728, 1616, 1528, 1325, 1127, 837, 672 cm-1; HRMS m/z (M+) calcd for C21H10F6O3: 424.0534. Found: 424.0532.

The synthetic route of 7270-63-5 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;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 426-65-3, name is Ethyl Pentafluoropropionate, This compound has unique chemical properties. The synthetic route is as follows., Quality Control of Ethyl Pentafluoropropionate

Pentafluoroethyl cyclopropylethynyl ketone, (XVI) can be synthesized in an analogous fashion using ethyl pentafluoropropionate in the above reaction.

According to the analysis of related databases, 426-65-3, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Pierce, Michael Ernest; Radesca, Lilian Alicia; US6348616; (2002); B1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 680217-71-4, name is Ethyl 2-(2,6-difluorophenyl)acetate, This compound has unique chemical properties. The synthetic route is as follows., HPLC of Formula: C10H10F2O2

General procedure: To a stirred solution of phenyl acetic acid ethyl ester 1a (1 g, 6.09 mmol) in THF (10 mL) was added LiHMDS (9.1 ml, 1 M sol. in THF, 7.31 mmol) at -78 C and the reaction mixture was stirred at this temperature for 30 min. Ethyl-1-imidazole carboxylate 2 (1.2 g, 9.146 mmol) in dry THF (3 ml) was added drop wise to the reaction mixture at -78 C and stirred at rt for 3 h. The reaction mixture was quenched with saturated ammonium chloride solution and extracted with ethyl acetate. The combined organic layer was washed with water, saturated brine solution, and dried over Na2SO4. The solvent was evaporated under reduced pressure and the crude product was chromatographed on a silica gel column. Elution with 4% ethyl acetate/pet ether gave the pure compound 3a (1.1 g, 81% yield) as a colorless liquid.

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 680217-71-4.

Reference:
Article; Behera, Manoranjan; Venkat Ragavan; Sambaiah; Erugu, Balaiah; Rama Krishna Reddy; Mukkanti; Yennam, Satyanarayana; Tetrahedron Letters; vol. 53; 9; (2012); p. 1060 – 1062;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

383-62-0, name is Ethyl 2-chloro-2,2-difluoroacetate, belongs to esters-buliding-blocks compound, is considered to be a conventional heterocyclic compound, which is widely used in drug synthesis. The chemical synthesis route is as follows. HPLC of Formula: C4H5ClF2O2

tert-Butyl 5-bromo-3-{(1S)-1-[2-chloro-6-(difluoromethoxy)-3-fluorophenyl]ethyl}-1H-pyrrolo[2,3-b]pyridine-1-carboxylate A mixture of tert-butyl 5-bromo-3-[(1S)-1-(2-chloro-3-fluoro-6-hydroxyphenyl)ethyl]-1H-pyrrolo[2,3-b]pyridine-1-carboxylate (1.00 g, 2.13 mmol), chlorodifluoroacetic acid ethyl ester (2.700 mL, 21.29 mmol), K2CO3 (882.7 mg, 6.387 mmol) and DMF (40 mL, 500 mmol) was heated to 70 C. for 6 h in a sealed tube. The material was extracted with EtOAc, and washed with water (3*). The organic layer was purified via column chromatography, eluting with 3-10% EtOAc/hexanes. The fractions containing the pure product were concentrated in vacuo to afford the title compound as a light yellow solid. 1H NMR (400 MHz, CD3OD): delta=1.67-1.69 (m, 9H), 1.80 (d, J=7.1 Hz, 3H), 4.94-5.03 (m, 1H), 6.63 (s, 1H), 7.15 (dd, J=9.1, 4.5 Hz, 1H), 7.22-7.28 (m, 1H), 7.55 (d, J=2.0 Hz, 1H), 7.70 (d, J=1.5 Hz, 1H), 8.34 (d, J=2.0 Hz, 1H). MS (ES+): m/z=519.03/521.03 (75/100) [MH+]. HPLC: tR=1.93 min (polar-3 min, HPLC-ACQUITY).

The synthetic route of 383-62-0 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; OSI Pharmaceuticals, LLC; US2011/281888; (2011); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 15963-40-3, 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. 15963-40-3, name is Methyl 3-methylenecyclobutanecarboxylate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below.

A dry three-neck flask was charged with methyl 3-methylenecyclobutanecarboxylate (6 g, 47.6 mmol) and dry THF (20 ml) and cooled to -10 C. BH3.THF (12.26 g, 143 mmol) was then added via a syringe dropwise. The resulting mixture was stirred for 4h at rt and was cooled to -20 C – 10C. Methanol was then added and the mixture was stirred for 15min. Sodium hydroxide (3M; 30 ml) and H2O2 (7.29 ml_, 238 mmol) were added in sequence. The mixture was stirred for 2h and a saturated sodium sulfite solution (100 ml) was added. The reaction mixture was diluted with water, then extracted with ethyl acetate, washed with water and brine, dried over sodium sulfate, filtered, and the residue was purified by flash chromatography eluting with (petroleum ether/EtOAc = 3/1 ) to afford methyl 3- (hydroxymethyl)cyclobutanecarboxylate (250 mg, 1 .387 mmol, 2.92 % yield) as a yellow oil.

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

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; GLAXOSMITHKLINE (CHINA) R&D COMPANY LIMITED; BARBE, Guillaume; BOHNERT, Gary; CALANDRA, Nicholas; LAMBERT III, Millard Hurst; LU, Hongfu; LOBERA, Mercedes; RAMANJULU, Joshi; REN, Feng; YANG, Ting; (337 pag.)WO2019/63748; (2019); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Synthetic Route of 39503-58-7, These common heterocyclic compound, 39503-58-7, name is Methyl 5-bromo-2-methoxy-4-methylbenzoate, 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 S2(12.8g, 48.8 mmol), N-bromosuccinimide (9.68 g, 54.78 mmol, 1.1 eq.), azobisisobutyronitrile (1.64 g, 9.96 mmol, 0.2 eq.) in carbon tetrachloride was heated at 70 C. After 14 h, solvent was removed and the residue purified by flash chromatography (Si02, 1 :9 ethyl acetate/hexanes) to afford S3 (13.92 g, 71.3 %) as a white amorphous solid. 1H NMR (500 MHz, CDC13) delta 7.91 (s, 1H), 7.60 (s, 1H), 7.00 (s, 1H), 3.99 (s, 3H), 3.90 (s, 3H).13C NMR (125 MHz, CDC13) delta 164.7, 159.0, 144.8, 135.5, 123.0, 114.6, 109.5, 56.7, 52.7, 39.3. HRMS (ESI+) m/z [M + H+] calcd for C10H11Br203, 336.9075, found 336.9079.

The synthetic route of 39503-58-7 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; UNIVERSITY OF KANSAS; BLAGG, Brian S. J.; KENT, Caitlin Nicole; MISHRA, Sanket Jaiprakash; (93 pag.)WO2018/132769; (2018); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

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. 6279-86-3, name is Triethyl methanetricarboxylate, This compound has unique chemical properties. The synthetic route is as follows., 6279-86-3

1b) 6-Hydroxy-2-phenyl-3-(phenylmethyl)-4(3H)-pyrimidinone; A mixture of the compound from example 1(a) (0.342 g, 1.63 mmol), triethyl methanetricarboxylate (0.755 g, 3.25 mmol), methanolic sodium methoxide (0.378 mL of a 4.37 M solution, 1.65 mmol) and ethanol (3 mL) was stirred in a microwave reactor at 160 C. for 0.5 h, then cooled and poured into 1M aqueous hydrochloric acid (20 mL). The mixture was extracted with ethyl acetate, and the extracts washed with brine, dried (MgSO4) and evaporated under reduced pressure. The residue was chromatographed (silica gel, 5-10% methanol/dichloromethane) to give the title compound (0.320 g, 44%) as a foam. 1H NMR (400 MHz, DMSO-d6) delta ppm 5.05 (s, 2 H) 5.50 (s, 1 H) 6.87 (m, 2 H) 7.18-7.26 (m, 3 H) 7.36-7.43 (m,4H) 7.49 (m, 1 H) 11.64 (s, 1 H).

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; Shaw, Antony N.; Duffy, Kevin J.; Tedesco, Rosanna; Wiggall, Kenneth; US2008/171756; (2008); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics

Adding a certain compound to certain chemical reactions, such as: 55666-43-8, name is tert-Butyl 3-bromopropanoate, 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 55666-43-8, Application In Synthesis of tert-Butyl 3-bromopropanoate

To a mixture of 2-sulfanyl-5,6,7,8-tetrahydro-4-quinazolinol (0.482 g, 2.64 mmol) and potassium carbonate (0.730 g, 5.29 mmol) in acetone was added tert-butyl 3-bromopropionate (0.663 g, 3.17 mmol). The mixture was stirred at 60C for 4 h (LC-MS indicated partial conversion to desired product). The solid was filtered off, and the solution was concentrated. The residual material was absorbed onto a plug of silica gel and purified by chromatography through a Redi-Sep pre-packed silica gel column (40 g), eluting with a gradient of 0% to 50% EtOAc in hexane, to provide tert- butyl 3-((4-oxo-3,4,5,6,7,8-hexahydroquinazolin-2-yl)thio)propanoate (0.132 g, 0.425 mmol, 16.09 % yield) as white solid. lH NMR (400 MHz, DMSO-i/6) delta ppm 12.40 (br. s., 1 H) 3.24 (t, J=6.70 Hz, 2 H) 2.64 (t, J=6.75 Hz, 2 H) 2.42 – 2.49 (m, 2 H) 2.28 (br. s., 2 H) 1.60 – 1.78 (m, 4 H) 1.41 (s, 9 H). m/z (ESI) 31 1.2.

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; AMGEN INC.; BREGMAN, Howard; BUCHANAN, John L.; CHAKKA, Nagasree; DIMAURO, Erin F.; GUNAYDIN, Hakan; GUZMAN PEREZ, Angel; HUA, Zihao; HUANG, Xin; WO2014/36022; (2014); A1;,
Ester – Wikipedia,
Ester – an overview | ScienceDirect Topics