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. 33689-29-1, name is Methyl 1-hydroxycyclopropanecarboxylate, This compound has unique chemical properties. The synthetic route is as follows., Product Details of 33689-29-1

Piperidine-1-carbonyl chloride (1.599 mL) was added to a solution of methyl 1-hydroxycyclopropanecarboxylate (1 mL) and DIEA (3.04 mL) in DCM (15 mL). The resulting solution was stirred at rt for 2 h, then diluted with DCM and the organic layer was wahed with iN HC1, water and brine, dried (Mg504), filtered andconcentrated. The residue was purified with silica gel gel to yield Cap L-7 Step a (0.75 g).

According to the analysis of related databases, 33689-29-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; BRISTOL-MYERS SQUIBB COMPANY; HEWAWASAM, Piyasena; LOPEZ, Omar D.; TU, Yong; WANG, Alan Xiangdong; XU, Ningning; KADOW, John F.; MEANWELL, Nicholas A.; GUPTA, Samayamunthula Venkata Satya Arun Kumar; KUMAR, Indasi J. Gopi; PUNUGUPATI, Suresh Kumar; BELEMA, Makonen; WO2015/5901; (2015); A1;,
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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. 40872-87-5, name is Methyl 3-amino-4-chlorobenzoate belongs to esters-buliding-blocks compound, it is a common compound, a new synthetic route is introduced below. Recommanded Product: 40872-87-5

In one example of the inventive process, the reaction was conducted with methyl 3-amino-4-chloro-benzoate and 1-cyclopentyl-2-pyridinyl acetylene as the starting materials (Scheme 7). Suitable choices of ligand, base and solvent was important for obtaining satisfactory results as shown in Table 1. Several ligands were examined. It was found that the reaction proceeded smoothly to afford the desired indole product when using either ligand 4a, 4b or 5 in the presence of n-Bu4N+OAc-. The major side-reaction was homocoupling of the arylchloride via double amination (entries 1-3). The proper choice of base, solvent, temperature, and concentration was important to minimize the formation of the amination byproduct and also maximize the desired regioselectivity. By using inorganic bases such as K2CO3, a cleaner reaction could be obtained than by using n-Bu4N+OAc- as base. When a ferrocene ligand such as bis(diisopropylphosphino)ferrocene was employed, in combination with K2CO3 as base, the indolization of 2-chloroaniline with the internal acetylene completed rapidly, providing the product in high purity and regioselectivity (entry 4). Addition of LiCl or LiI as additive did not improve the yield. Instead, it slowed down the reaction (entries 5-6). With reduced catalyst loading (5 mol %), the reaction also proceeded smoothly and cleanly (entry 7). Changing the ratio of ligand to palladium acetate from 2:1 to 1:1 prolonged the reaction time (entry 8). Using K2CO3 as base, ligands 4a, 4b or 6 also afforded good results (entries 9-10). The wavelength used was 240 nm. TABLE I Base Time Entry (Scale) (eq) Catalyst (h) Result* 1 (100 mg) n-Pd(OAc)2 (10%) 4 Complete conversion of Bu4N+OAc- 2-(Di-t- starting material, giving 45 (2.5 eq) butylphosphino)- area % product and 33 biphenyl (40%) area % byproduct. 2 (100 mg) n-Pd(OAc)2 (10%) 3 Ratio of the desired product Bu4N+OAc- 1,1′- to starting material (2.5 eq) Bis(diphenylphosphino) (cholroaniline) was 5:1, ferrocene(20%) about 35 area % unknown impurities. The ratio of the regioisomers was 9:1. 3 (200 mg) n-Pd(OAc)2 (10%) 14 Complete conversion of the Bu4N+OAc- 1,1′-Bis(di-i- starting material, about 35 (2.5 eq) propylphosphino) area % of unknown ferrocene(20%) impurities. The ratio of the regioisomers was 9:1. 28% isolated yield was obtained through column chromatography for two steps. 4 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 3 Complete conversion of the 1,1′-Bis(di-i- starting material. The propylphosphino) desired product was formed ferrocene(20%) in 88 area % purity. The ratio of the regioisomers was 20:1. 5 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 Ratio of the desired product 1,1′-Bis(di-i- to the starting material was LiCl (1 eq) propylphosphino) 14:1. The ratio of the ferrocene(20%) regioisomers was 19:1. 6 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (10%) 5 The ratio of the desired 1,1′-Bis(di-i- product to the starting LiI (1 eq) propylphosphino) material was 1.6:1. ferrocene(20%) 7 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 5:1. The ratio ferrocene(10%) of regioisomers was 18:1. 8 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired 1,1′-Bis(di-i- product to the starting propylphosphino) material was 2.5:1. The ferrocene(6%) ratio of regioisomers was 19:1. 9 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 Complete conversion of the 2-(Di-t- starting material, with about butylphosphino)- 20 area % impurities. The biphenyl (10%) ratio of the regioisomers was 20:1. 10 (100 mg)K2CO3 (2.5 eq)Pd(OAc)2 (5%) 14 The ratio of the desired Tricyclohexylphosphine product to the starting (10%) material was 4:1. Ratio of the regioisomers was 18:1. *Ratios of product were measured by HPLC analysis

The synthetic route of 40872-87-5 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Boehringer Ingelheim International GmbH; US2005/209465; (2005); A1;,
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Electric Literature of 7515-17-5,Some common heterocyclic compound, 7515-17-5, name is Methyl 3-(4-methoxyphenyl)propiolate, molecular formula is C11H10O3, 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 2.2 3- (4-Methanesulfonvl-phenvl)-2- (4-methoxv-phenyl)-pyrazolof 1. 5-blpyridazine (i) 2-(4-Methoxy-phenyl)-pyrazolo[1,5-b]pyridazine-3-carboxylic acid methyl ester Diazabicyclo [5.4. 0] undec-7-ene (22.76mL, 2eq) was added dropwise to a solution of methyl 3- (4-methoxy-phenyl)-prop-2-ynoic acid’ (14. 46g, 76mM) and 1-aminopyridazinium iodide2 (2eq) in acetonitrile under nitrogen and stirred for 6h. Purification by chromatography on silica gel eluting with toluene, then toluene : ethyl acetate (9: 1) gave the title compound (2.76g) as a brown solid.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route Methyl 3-(4-methoxyphenyl)propiolate, its application will become more common.

Reference:
Patent; GLAXO GROUP LIMITED; WO2005/48999; (2005); A2;,
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Adding a certain compound to certain chemical reactions, such as: 3195-24-2, name is Diethyl 2,2-diallylmalonate, 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 3195-24-2, Product Details of 3195-24-2

Example 6: Comparison of Standard Activity Tests of the Ruthenium tetrasubstituted NHC complex H6 (see Example 3f) to the Ruthenium gem di-substituted NHC complex H8 (see Example 3h) for Ring Closing Metathesis (RCM), Cross Metathesis (CM) and Ring-Opening Metathesis Polymerization (ROMP) reactions. [0098] Example 6a. RCM Reactions: All tests were performed according to the experimental procedure described by Ritter et al. (see Ritter, T.; Heji, A.; Wenzel, A.; Funk, T. W. ; Grubbs, R. H., Organometallics, 2006, 25, 5740.) See Figure 7a, 7b and 7c. CD2CI2, 300C C6D6, 60uC(%)EtO2C CO2Et EtO2C CO2Et Catalyst Ytefd catalyst (1 mo. %)1) solvent, temperature O HO 99% {30 mi?) v-_. – / H6 95% (2h) 98% (5 mm)R7 R8 H8 95% (4h) 95% (10 min) EtO2C CO2Et EtO2C CO2EtHO 6% (96h) 30% (24 min) catalyst (5 mol %) H6 95% (4h) 98% {20 min)3) X ^?~ h P=^r ssoollvveenntt,, t teemmppeerraattuurree y H O H8 no reaction 55% (31 h)R11 R12

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, Diethyl 2,2-diallylmalonate, other downstream synthetic routes, hurry up and to see.

Reference:
Patent; MATERIA, INC.; CALIFORNIA INSTITUTE OF TECHNOLOGY; WO2009/126831; (2009); A1;,
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Application of 6642-30-4, A common heterocyclic compound, 6642-30-4, name is Methyl methylcarbamate, molecular formula is C3H7NO2, 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 10 2-SEC BUTYLPHENYL N-METHYLCARBAMATE To a mixture of methyl N-methylcarbamate (0.89 g, 0.01 mole) and 2-sec butylphenol (1.5 g, 0.01 mole) in dichloroethane (10 ml), a solution of phosphorus tribromide (2.7 g, 0.01 mole) in dichloro-ethane (6 ml) was added and the mixture was refluxed for eight hours. It was then worked up and purified as described earlier to give 2-sec butylphenyl N-methylcarbamate of the formula (III).

The synthetic route of 6642-30-4 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Council of Scientific & Industrial Research; US5066819; (1991); A;,
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These common heterocyclic compound, 14920-81-1, name is Methyl 2,6-dimethylbenzoate, 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. Computed Properties of C10H12O2

General procedure: To a flame-dried 250 mL round-bottom flask under argon wereadded 4 (8.02 g, 28.4 mmol, 1 equiv), TMEDA (8.71 mL, 58.2mmol, 2.05 equiv), and anhydrous n-hexane (28 mL). Theresulting solution was cooled in an ice bath and sec-butyllithium(1.4 M solution in cyclohexane, 42.0 mL, 58.2 mmol, 2.05equiv) was added dropwise. The ice bath was removed and thereaction mixture was stirred at room temperature for 4 h. Thereaction was cooled to -78 C and a solution of methyl 2,4,6-trimethylbenzoate (5.11 g, 28.7 mmol, 1.01 equiv) in anhydrousn-hexane (28 mL) was added slowly via cannula. After the addition,the mixture was allowed to slowly warm to room temperatureand stirred for 12 h. The reaction was quenched with water(25 mL) and the biphasic mixture was stirred vigorously for 30min. The mixture was diluted with Et2O (100 mL) and the layerswere separated. The organic layer was washed with water(2 × 150 mL) and brine (1 × 150 mL). The organic layer wastransferred to a 250 mL round-bottom flask equipped with astir bar. To the vigorously stirred solution was added conc. HCl(12 mL), resulting in a bright-yellow precipitate. The suspensionwas stirred vigorously for 30 min then diluted with water (150mL). The layers were separated and the organic layer wasextracted with water (3 × 150 mL or until the washings becomecolorless). To the combined aqueous layers was added solidNaBF4 (9.35 g, 85.2 mmol, 3 equiv), resulting in a bright-yellowprecipitate. The resulting suspension was extracted withdichloromethane (3 × 150 mL or until the washings become colorless).To the combined organic layers was added HBF4·Et2Ocomplex (3.46 mL, 28.4 mmol, 1 equiv). The solution wasswirled to achieve homogeneity then washed with water(1 × 100 mL) and aq. NaBF4 (1 M, 1 × 100 mL). The organic layerwas dried over solid NaBF4, filtered, and concentrated to dryness.The residue was purified by trituration with hexanes andfiltered. The solid was rinsed with n-pentane and dried in vacuoto give xanthylium 3 (10.6 g, 21.3 mmol, 75% yield) as a yelloworangesolid.

The synthetic route of Methyl 2,6-dimethylbenzoate has been constantly updated, and we look forward to future research findings.

Reference:
Article; White, Alexander R.; Wang, Leifeng; Nicewicz, David A.; Synlett; vol. 30; 7; (2019); p. 827 – 832;,
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These common heterocyclic compound, 1070-64-0, name is Ethyl 6,8-dichlorooctanoate, 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. name: Ethyl 6,8-dichlorooctanoate

1, 100 g (0.4mol) racemic Ethyl 6, 8-Dichlorooctanoic acid (95% industrial grade) is prepared first, and then treated with an alkali hydrolysis process so as to obtain (+/-)-DCA 80 g, to be dissolved into 300 ml ethyl acetate, followed by 24 g (0.2 mol) S-(-)-alpha-phenethylamine, afterwards, gradually cooled down to a temperature range between 0-10 C., overnight, filtered, and ultimately obtain 30 g wet (+)DCA S-(-)-alpha-phenethylamine salt. Afterwards, a recrystallization process is followed, wherein the (+)DCA-S-(-)-alpha-phenethylamine salt is dissolved in the ethyl acetate, and acidified with diluted hydrochloric acid, and extracted by methylbenzene, and distilled at low temperature to remove solvent, finally obtain 18.8 g (+)-DCA, [alpha]D25+48-49.6 with a yield rate from 42% to 46%.

The synthetic route of Ethyl 6,8-dichlorooctanoate has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Nanjing Rally Biochemical Inc.; US2007/15926; (2007); A1;,
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Adding a certain compound to certain chemical reactions, such as: 2672-58-4, name is Trimethyl benzene-1,3,5-tricarboxylate, 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 2672-58-4, name: Trimethyl benzene-1,3,5-tricarboxylate

a solution of triphenylphosphine (577 mg, 2.2 mmol) in anhydrous THF (5 mL) was added diethyl azodicarboxylate (2.2 M in toluene, 791 muL, 1.7 mmol) dropwise at 0C. After stirred at 0C for 50 minutes, a solution of 1,3,5-tri(hydroxymethyl)benzene (269 mg, 1.6 mmol, prepared by reduction of trimethyl 1,3,5-benzenetricarboxylate with lithium aluminum hydride in THF, co-evaporated with dry benzene and dried on high vacuum for couple hours before use) and thioacetic acid (108 muL, 1.45 mmol) in dry THF (4 mL) was added dropwise. After 1 hour, the ice/water bath was removed and the reaction was stirred at room temperature for 15 hours. The solvents were removed by rotary evaporation in vacuo. The residue was purified by flash chromatography to give 5-acetylthiomethyl-1,3-bis(hydroxymethyl)-benzene as colorless solid (110 mg). 1H NMR (400 Hz, CDCl3): delta 7.13-6.99 (m, 3H), 4.45 (apt, J = 20.4 Hz, 4H), 3.98 (apt, J = 20.4 Hz, 4H), 3.73 (bs, 2H), 2.24 (apt, J = 20.4 Hz, 3H); MS (ESI): m/z 249.0 (M + Na)+.

At the same time, in my other blogs, there are other synthetic methods of this type of compound, Trimethyl benzene-1,3,5-tricarboxylate, and friends who are interested can also refer to it.

Reference:
Patent; Sanofi-Aventis; EP1813614; (2007); A1;,
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Electric Literature of 18014-00-1, A common heterocyclic compound, 18014-00-1, name is Dimethyl 2,5-dibromoterephthalate, molecular formula is C10H8Br2O4, 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 1] A mixed liquid of methyl p-dibromoterephthalate (Compound 1)(9.86 g, 28 mmol) synthesised according to the method of a literature (), sodium 2-hexylthiophene-5-borate (Compound 2)(15.5 g, 61.6 mmol) synthesised according to the method of a literature (), PdCl2(dppf)·CH2Cl2 (1.83 g, 2.24 mmol), and toluene (1 L) was refluxed under a nitrogen atmosphere for 9 hours. After the reaction mixed liquid was allowed to cool to room temperature, water was added to the reaction mixed liquid and the reaction mixed liquid was subjected to extraction with chloroform. The obtained organic layer was dried with sodium sulfate, and filtered, and thereafter, the solvent was distilled out under reduced pressure. The obtained mixture was separated and refined by a silica gel column chromatography to obtain dimethyl 2,5-bis(5-hexyl-2-thienyl)terephthalate (Compound 3)(10.8 g, 20.5 mmol) in a yield of 73%. The physical properties of dimethyl 2,5-bis(5-hexyl-2-thienyl)terephthalate (Compound 3) were as follows. 1H-NMR (CDCl3, delta ppm): 7.61 (s, 2H), 7.06 (d, 2H), 6.86 (d, 2H), 3.76 (s, 6H), 2.82 (t, 4H), 1.63-1.80 (m, 4H), 1.28-1.45 (m, 12H), 0.90 (t, 6H)

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; Sumitomo Chemical Company, Limited; EP2248818; (2010); A1;,
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Some common heterocyclic compound, 326-58-9, name is Benzo[d][1,3]dioxol-5-yl acetate, molecular formula is C9H8O4, 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. Computed Properties of C9H8O4

Acetic acid benzo[1,3]dioxol-5-yl ester 15 (2.51g, 13.93mmol) was dissolved in glacial acetic acid (5mL), then a solution of concentrated HNO3 1.1mL (70%, d=1.413, 1.09g, 17.27mmol) in glacial acetic acid (2mL) was added dropwise. The reaction mixture was stirred at rt for 4h, then was cooled at 0C. The yellow solid was filtrated, washed with cold water, air-dried, and used in the next step without further purification (2.95g, yield 94%). 1H NMR (300MHz, CDCl3) delta: 2.37 (s, 3H), 6.15 (s, 2H), 6.65 (s, 1H), 7.60 (s, 1H).

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route 326-58-9, its application will become more common.

Reference:
Article; Brogi, Simone; Ramunno, Anna; Savi, Lida; Chemi, Giulia; Alfano, Gloria; Pecorelli, Alessandra; Pambianchi, Erika; Galatello, Paola; Compagnoni, Giulia; Focher, Federico; Biamonti, Giuseppe; Valacchi, Giuseppe; Butini, Stefania; Gemma, Sandra; Campiani, Giuseppe; Brindisi, Margherita; European Journal of Medicinal Chemistry; vol. 138; (2017); p. 438 – 457;,
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