Category: alcohols-buliding-blocks

Adding a certain compound to certain chemical reactions, such as: 162744-59-4, (4-Bromo-2,6-difluorophenyl)methanol, 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, 162744-59-4, blongs to alcohols-buliding-blocks compound. name: (4-Bromo-2,6-difluorophenyl)methanol

General synthetic method 2: Borylation of arylbromides and subsequent Suzuki coupling with 5-bromopyrrolo[2,l-f][l ,2,4]- triazine derivatives without isolation of the intermediate arylboronic acid or ester: Arylbromide D (about 0.5 mmol) is dissolved in DMF (3 mL) in a microwave reactor vessel, argon is bubbled through the solution for 5 min, and [l ,l’-bis(diphenylphosphino)ferrocene]dichloro- palladium(II)-dichloromethane complex (0.1 equivalents), potassium acetate (3 equivalents) and bis(pinacolato)diboron (1.2 equivalents) are added. The vessel is crimp-capped, and the mixture is heated to 130C for 60 min in a single-mode microwave device. Then, the suspension is filtered, the filtrate is transferred to another microwave process vial, and tetrakis(triphenylphosphine)- palladium(O) (0.1 equivalents), 2 M aqueous sodium carbonate solution (4 equivalents) and the 5-bromopyrrolo [2, 1 -f] [ 1 ,2,4]triazine A (1 equivalent) are added. The vial is crimp-capped, and the mixture is heated to 140C for 1 h in a single-mode microwave device. The crude reaction mixture thus obtained is directly injected onto a preparative HPLC column for separation and purification of the target compound C.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,162744-59-4, its application will become more common.

Reference:
Patent; BAYER INTELLECTUAL PROPERTY GMBH; Bayer Pharma Aktiengesellschaft; KLAR, Juergen; VOEHRINGER, Verena; TELSER, Joachim; LOBELL, Mario; SUessMEIER, Frank; LI, Volkhart Min-Jian; BOeTTGER, Michael; GOLZ, Stefan; LANG, Dieter; SCHLEMMER, Karl-Heinz; SCHLANGE, Thomas; SCHALL, Andreas; FU, Wenlang; WO2013/4551; (2013); A1;,
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Application of 1562-00-1, 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. 1562-00-1, name is Sodium isethionate, molecular formula is C2H5NaO4S, The 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.

Reaction product V, [C1impd]2[SO4] (3.166 g, 8.74 mmol) was dissolved in 2:1 alcohol-water (30 mL), whereupon a prepared solution of sodium isethionate (2.592 g, 17.50 mmol) in 2:1 alcohol-water (18 mL) was added to it with stirring. The resulting slurry was stirred for about 2 h, whereupon it was suction filtered, and the filtrate was concentrated as far as feasible by rotary evaporation. The residue was taken up in methanol (25 mL) and loaded onto an about 12-g column of 230-400 mesh silica gel previously packed in methanol.As in Example 3, the methanolic solution of crude [C1impd][ise] was pushed down to the level of the top of the silica gel bed with air pressure while the column issue was collected in a 250-mL round bottom flask; the flask previously containing the crude product was rinsed with methanol (25 mL) and the rinse methanol was similarly loaded and pressed down while the column issue was collected on top of the first fraction. The rinsing process was repeated once before the silica gel column was washed down with fresh methanol (125 mL), all the while collecting the column issue on top of the accumulated methanol solution. The combined methanolic fractions were concentrated by rotary evaporation to produce purified [C1impd][ise] (4.122 g, 15.96 mmol, 91%) as an ionic liquid. The ionic liquid of Example 11 slowly solidified at ambient conditions. Specifically, it was freely liquid when contained in a flask immersed in an 80 C. water bath; it remained liquid for several hours after it was removed from the water bath. Thereafter, several regions of the liquid began to slowly solidify independently of each other, and after about 1 day, the IL had turned thoroughly solid under ambient conditions.

According to the analysis of related databases, 1562-00-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; FLUIDIC, INC.; US2012/321967; (2012); A1;,
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Electric Literature of 6351-10-6 , The common heterocyclic compound, 6351-10-6, name is 2,3-Dihydro-1H-inden-1-ol, molecular formula is C9H10O, 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.

DMAP (143.8 mg, 1.25 mol) and acetic anhydride (1185.6 L,12.48 mmol) were added to a rac-indanol (rac-2), 500 mg,4.16 mmol) solution in dichloromethane (40 mL). The reaction wasstirred at room temperature during 4 h and after that time, thesolvent was evaporated under reduced pressure. The resultingcrude was purified by flash chromatography on silica gel (5-95%EtOAc/hexane) to afford the desired rac-indanyl acetate (rac-3) asa yellow liquid in 80% yield.

The synthetic route of 6351-10-6 has been constantly updated, and we look forward to future research findings.

Reference:
Article; De Mattos, Marcos Carlos; De Fonseca, Thiago Sousa; Da Silva, Marcos Reinaldo; De Oliveira, Maria Da Conceicao Ferreira; De Lemos, Telma Leda Gomes; De Marques, Ricardo Araujo; Applied Catalysis A: General; vol. 492; 1; (2015); p. 76 – 82;,
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Related Products of 23783-42-8, The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. This compound has unique chemical properties. The synthetic route is as follows.

Step 1: [chloromethyl 2,5,8,11-tetraoxatridecan-13-yl carbonate] To a stirred solution of chloromethyl carbonochloridate (2.6 g, 20 mmol) in dichloromethane (40 mL) was added a mixture of 2,5,8,11-tetraoxatridecan-13-ol (4.16 g, 20 mmol) and triethylamine (2 g, 20 mmol) in dichloromethane (5 ml) dropwise at 0 C. The resulting reaction mixture was stirred at 0 C. for 0.5 hour. TLC showed the reaction was completed. The reaction mixture was partitioned between tert-Butyl methyl ether (100 ml) and water (60 ml). The organic layer were collected, washed with brine (50 ml), dried over anhydrous sodium sulfate, and concentrated under reduced pressure to give a crude residue which was purified by silica gel flash chromatography (eluted with 30% ethyl acetate in hexane) to afford chloromethyl 2,5,8,11-tetraoxatridecan-13-yl carbonate (2.2 g, yield 35.2%) as colorless oil. 1H NMR (400 MHz, CDCl3): delta 3.38 (s, 3H), 3.54-3.56 (m, 2H), 3.64-3.66 (m, 10H), 3.74-3.76 (m, 2H), 4.36-4.38 (m, 2H), 5.74 (s, 2H).

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol.

Reference:
Patent; Arvinas, Inc.; Crew, Andrew P.; Hornberger, Keith R.; Snyder, Lawrence B.; Zimmermann, Kurt; Wang, Jing; Berlin, Michael; Crews, Craig M.; Dong, Hanqing; (605 pag.)US2018/99940; (2018); A1;,
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Adding a certain compound to certain chemical reactions, such as: 16545-68-9, Cyclopropanol, 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, Formula: C3H6O, blongs to alcohols-buliding-blocks compound. Formula: C3H6O

A mixture of 2-bromo-6-fluoropyridine (371 mg, 2.1 mmol) and cyclopropanol (350 mg, 6.0 mmol) in NMP (6 mL) was stirred for 5 minutes at 0 oC. Then to the solution was added dropwise a solution of t-BuOK in THF (1M, 0.6 mL, 0.6 mmol) at 0 oC. After addition, the reaction mixture was warmed to RT and stirred for 2 h. The reaction mixture was poured into a mixed solvent of PE/EA/water (50 mL/50mL/100 mL). The organic layer was separated, washed with 5% of LiCl aqueous solution (20 mL), dried over anhydrous Na2SO4, and filtered. The filtrate was concentrated in vacuo, and the residue was purified by silica gel column (5% ~ 10% EA/PE) to afford 2-bromo-6-cyclopropoxypyridine (374 mg, 83%) as a colorless oil. LC- MS m/z: 216&218 [M+H]+. Purity (214 nm): 99.6%.

The synthetic route of 16545-68-9 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; LYSOSOMAL THERAPEUTICS INC.; SKERLJ, Renato, T.; BOURQUE, Elyse Marie Josee; LANSBURY, Peter, T.; GREENLEE, William, J.; GOOD, Andrew, C.; (309 pag.)WO2017/176961; (2017); A1;,
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The major producers of chemicals have been the Europe, Japan and China. Due to the growing call for a cleaner, greener environment, people will have to find innovative ways to maintain their relevance. Here is a compound 3637-61-4, name is Cyclopentanemethanol. This compound has unique chemical properties. The synthetic route is as follows. Application In Synthesis of Cyclopentanemethanol

Synthesis of methyl 3- (4-CYCLOPENTYLMETHYLOXYPHENYL) propionate (Intermediate 2); A solution of cyclopentane methanol (4.05 ml, Ald) in anhydrous tetrahydrofuran (abbreviated as”THF”hereinafter, 40 ml) was added with triethylamine (6.49 ml, WAKO), added dropwise with methanesulfonyl chloride (3.48 ml, WAKO) under ice cooling, and stirred for 30 minutes. The reaction mixture was added with water (50 ml), and extracted with diethyl ether (80 ml X 2). The organic layer was washed with saturated brine and dried, and then the solvent was evaporated under reduced pressure. A solution obtained beforehand by adding 60% sodium hydride (1.15 g, KANTO) to a solution of Intermediate 1 (4.50 g) in N, N-dimethylformamide (abbreviated as”DMF”hereinafter, 35 ml) under ice cooling and stirring the solution for 15 minutes was added with a solution of the aforementioned residue in DMF (10 ml) under ice cooling. The reaction mixture was stirred for 15 minutes, then warmed to room temperature, stirred for 45 minutes, and further stirred at 60C for 15 hours. The reaction mixture was added with water (100 ML) and diethyl ether (200 ml) for extraction. The organic layer was successively washed with saturated aqueous sodium hydrogencarbonate, saturated aqueous ammonium chloride, and saturated brine and dried, and then the solvent was evaporated under reduced pressure. The residue was purified by flash column chromatography (hexane : isopropyl ether = 9: 1) to obtain the title compound (Intermediate 2,5. 58 G).

With the rapid development of chemical substances, we look forward to future research findings about 3637-61-4.

Reference:
Patent; ASAHI KASEI PHARMA CORPORATION; WO2005/16862; (2005); A1;,
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Synthetic Route of 6301-54-8, 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 6301-54-8 as follows.

General procedure: In a round bottom ask tted with three-way cock with septumwas placed benzyl alcohol analogue (1.0e1.5 mmol). The ask waslled with nitrogen after reducing pressure. After slight decom-pression to ease to the gas introduction, HI gas (0.5e2.0 equiv.) wasbrought in the vessel with syringe through the septum (the weightof HI gas was calculated the change of the weight of the equipmentbefore and after the introduction of HI gas). And nitrogen gas wasintroduced into vessel to release deference of pressure against at-mosphere. The mixture stood at 25C for 2 d. After reducingpressure to release HI gas, to the reaction mixture was addedsaturated Na2S2O3 (20 mL) and brine (15 mL). After being extractedwith CHCl3 or Et2O (15 mL 3), the organic layer was dried withMgSO4. After the concentration, ca. 10.0 mg of the residue wascombined with p-chlorobenzaldehyde (ca. 10.0 mg) as an internalstandard. And the mixture was measured with1H NMR to deter-mine the yield by the integration of methyl, methylene or methinepeak of the product and formyl peak of p-chlorobenzaldehyde(9.98 ppm). Furthermore, the reaction mixture included in p-chlorobenzaldehyde was subject to column chromatography onSiO2 to give the product.Iodinated products, (iodomethyl)benzene (2a),29(1-iodoethyl)benzene (2b),30and reduction products, diphenylmethane (3d),311,1-diphenylethane (3e),32triphenylmethane (3f),33wereassigned by the corresponding proton peaks at benzylic positionscompared with the chemical shift reported in the literature.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,6301-54-8, its application will become more common.

Reference:
Article; Matsumoto, Shoji; Naito, Masafumi; Oseki, Takehisa; Akazome, Motohiro; Otani, Yasuhiko; Tetrahedron; vol. 73; 52; (2017); p. 7254 – 7259;,
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Electric Literature of 100-37-8, 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. 100-37-8, name is 2-(Diethylamino)ethanol, molecular formula is C6H15NO, The 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.

diethylaminoethyl methacrylate is synthesized by using diethylaminoethanol and methyl methacrylate as raw materials and lithium hydroxide as a catalyst. The process steps are as follows:(1) Synthesis: 300 g (3.0 mol) of methyl methacrylate, 117 g (1.0 mol) of diethylaminoethanol, 10 g of lithium hydroxide and 0.6 g of hydroquinone were added to a 1000 mL with stirring, a thermometer and a vacuum fractionation apparatus. The three-necked flask was heated to 75 C to 85 C, and the temperature at the top of the column was controlled to be 50 C to 55 C. The methanol was continuously separated under a negative pressure of about 600 mmHg, and the reaction was stopped until no methanol was separated (about 3.5 h). Methanol 33.0 g was separated, and gas chromatographic analysis showed that the methanol content was 89.3% and the methyl methacrylate content was 9.6%.(2) Purification: Cool to room temperature and wash twice with 300 mL × 2 of deionized water. The oil phase is gradually depressurized (40-100 mmHg), and unreacted methyl methacrylate and diethylaminoethanol are distilled off at 70 C to 100 C, and then distilled under reduced pressure at 5 to 10 mmHg and 90 C to 100 C. Diethylaminoethyl acrylate. The weight of the obtained mixture of methyl methacrylate and diethylaminoethanol was 195.8 g, and gas chromatographic analysis showed that the methyl methacrylate content was 95.9% and the diethylaminoethanol content was 3.6%. This mixture can be used directly for the synthesis of diethylaminoethyl methacrylate. The weight of the obtained product was 174.1 g (theoretical yield: 185.26 g), and the yield was 94.0%. The gas chromatographic analysis showed that the content of diethylaminoethyl methacrylate was 99.4%.

While traditionally a conservative industry, chemical producers will need to modernize their PR strategies to stay relevant.we look forward to future research findings about 100-37-8, 2-(Diethylamino)ethanol.

Reference:
Patent; Sinopec Corporation; Sinopec Corporation Victory Oil Field Fen Corporation Petroleum Engineering Technology Institute; Zhang Songting; Yang Shengli; Bai Xin; Rong Yan; Du Chunan; Chen Xiaochun; Cai Qingjun; Ma Tiantai; Sun Lizhu; Yue Jiwen; (10 pag.)CN108976136; (2018); A;,
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Application of 627-27-0 ,Some common heterocyclic compound, 627-27-0, molecular formula is C4H8O, 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.

Intermediate 38. [0131] NaH (50% in oil, 2.88 g, 0.06 mol) was slowly added to a solution of Intermediate 37 (3 g, 0.041 mol) in 30 mL anhydrous DMF in ice-bath. After stirring for 0.5 h, BnBr (5.38 mL, 0.045 mol) was added to the reaction solution and stirred at r.t. for overnight. The mixture was poured into 80 mL H2O at 0 C., extracted with EtOAc. The combined organic phase was washed with aq. NH4Cl, brine and dried over Na2SO4. After concentration, the residue was dissolved in PE (petroleum ether), and filtered through a pad of silica gel. The filtrate was concentrated to afford the Intermediate 38 as colorless oil.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,627-27-0, its application will become more common.

Reference:
Patent; MICURX PHARMACEUTICALS, INC.; GORDEEV, Mikhail Fedorovich; LIU, Jinqian; YUAN, Zhengyu; WANG, Xinghai; US2013/165411; (2013); A1;,
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Adding a certain compound to certain chemical reactions, such as: 7218-43-1, 2-[2-(2-Propynyloxy)ethoxy]ethanol, 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, Recommanded Product: 7218-43-1, blongs to alcohols-buliding-blocks compound. Recommanded Product: 7218-43-1

Intermediate 3: 2-(2-(prop-2-ynyloxy)ethoxy)ethylcarbamateTo a solution of 2-(2-(prop-2-yn-1-yloxy)ethoxy)ethan-1-ol (8.99 mmol) in dry DCM (50 ml), was added2,2,2-trichloroacetyl isocyanate (10.79 mmol) at 0 C. After 1 hour stirring at room temperature, thesolvent was evaporated and the reaction mixture was dissolved in 30 ml MeOH en 3 ml Water. K2C03(15.46 mmol) was added and the reaction was allowed to stir overnight. MeOH was evaporated andwater (50 ml) was added. This water layer was extracted twice with EtOAc. The organic layers were combined, washed with brine, dried over anhydrous Na2SO4, filtered and evaporated. A yellow oily liquid was obtained.Yield: 74% (1.2 g), MS (ESI) m/z 226 [M÷K]1H-NMR (ODd3, 400 MHz)6 2.40 (t, J=2.4 Hz, 1H), 3.65 (m, 6H), 4.20 (m, 4H), 4.90 (brs, 2H)

At the same time, in my other blogs, there are other synthetic methods of this type of compound,7218-43-1, 2-[2-(2-Propynyloxy)ethoxy]ethanol, and friends who are interested can also refer to it.

Reference:
Patent; UNIVERSITEIT ANTWERPEN; JOOSSENS, Jurgen; AUGUSTYNS, Koen; LAMBEIR, Anne-Marie; VAN DER VEKEN, Pieter; VAN SOOM, Jeroen; MAGDOLEN, Viktor; (66 pag.)WO2015/144933; (2015); A1;,
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