Category: 23783-42-8

Synthetic Route of 23783-42-8, 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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, 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.

2,5,8,1 1-Tetraoxatridecan-13-ol (5.0 g, 24.01 mmol) was dissolved in THF(20.01 ml). pyridine (5.83 ml, 72.0 mmol) was added to the mixture followed by 4-methylbenzene-1-sulfonyl chloride (5.49 g, 28.8 mmol). The mixture stirred at roomtemperature overnight. Mixture was concentrated by roto-vap. Residue was dissolved in dichloromethane. Material was washed twice with saturated aqueous sodium bicarbonate. Combined aqueous layers were back-extracted with dichloromethane. Combined organics were washed twice with iN hydrochloric acidand once with brine. Organics were dried MgSO4, filtered and then concentrated todryness to get 2,5,8,11-tetraoxatridecan-13-yl 4-methylbenzenesulfonate (4.12 g, 11.37 mmol, 47.3 % yield) which was used as is in the next step.

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; BRISTOL-MYERS SQUIBB COMPANY; GILLMAN, Kevin W.; GOODRICH, Jason; BOY, Kenneth M.; ZHANG, Yunhui; MAPELLI, Claudio; POSS, Michael A.; SUN, Li-Qiang; ZHAO, Qian; MULL, Eric; GILLIS, Eric P.; SCOLA, Paul Michael; LANGLEY, David, R.; (683 pag.)WO2016/77518; (2016); 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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. This compound has unique chemical properties. The synthetic route is as follows. name: 2,5,8,11-Tetraoxatridecan-13-ol

Tetraethyleneglycol monomethyl ether (1 .91 ml, 9 mmol) dissolved in dry and degassed DMF (3.5 ml, dried 24 h, 4A MS) was added carefully to sodium hydride (365 mg, 9 mmol) in dry and degassed DMF (15 ml, dried 24 h, 4A MS) under nitrogen at 0 C using a syringe. The temperature was then raised to room temperature and the reaction mixture was stirred for another 30 min. 3-(3-bromo-2,2-bis(bromomethyl)propoxy)prop-1 -ene (730 mg, 2.0 mmol) was then added and the temperature was raised to 100 C. After 14 h the reaction was completed (HPLC-ELSD-C18, 95:5 to 5:95 H2O/ACN in 25 min, Rt product = 19.5 min) the temperature was decreased to room temperature and the reaction mixture was carefully added to H2O (150 ml) and the H2O-phase was washed with diethyl ether (2 x 50 ml). Sodium chloride was then added to the H2O-phase until saturation. The H2O-phase was extracted with EtOAc (4 x 50 ml) and the combined organic phases were washed with brine (2 x 30 ml). Sodium sulfate and charcoal was added to the organic phase. The clear organic phase was filtered and the volatile material was removed at reduced pressure (8 mm Hg, 40 C then 0.1 mm Hg (oil pump) and 40 C to remove residual DMF). Column chromatography (EtOAc:MeOH 9:1 ) gave 1 .05 g (70%) of the product. 1H-NMR (CDCI3); 5.90 (m, 1 H), 5.20 (m, 2H), 3.94 (dt, 2H), 3.70-3.55 (m, 48H), 3.45 (s, 6H), 3.43 (s, 2H), 3.40 (s, 9H).

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, 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol.

Reference:
Patent; SPAGO IMAGING AB; AXELSSON, Oskar; PETORAL JR., Rodrigo M.; EK, Fredrik; LAURITZSON, Petter; WO2013/41623; (2013); A1;,
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With the rapid development and complex challenges of chemical substances, the synthesis of new drugs is usually one of the most effective ways to increase yield.23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, molecular weight is 208.25, as common compound, the synthetic route is as follows.SDS of cas: 23783-42-8

A THF solution (200 mL) of H(OCH2CH2)4OMe (12 g, 60 mmol) and a stir bar was placed in a threenecked flask (500 mL). NaH (60%, dispersion in Paraffin Liquid, 2.9 g, 72 mmol) was added to the solution, and the mixture was stirred at room temperature for 30 min. Allyl bromide (6.2 mL, 72 mmol) was slowly added to the resulting mixture at the same temperature with vigorous stirring. The solution was stirred overnight, and the remaining NaH and NaBr were filtered off. The obtained filtrate was concentrated to dryness in vacuo. The residue was dissolved in water (500 mL) and extracted with hexane (200 mL3) and then dichloromethane (200 mL3). The resulting organic layer was dried with MgSO4 and then further dried under vacuum to afford the title compound 1d as a colorless oil (14 g, 55 mmol, 92%) 1d: 1H NMR (600 MHz, C6D6): delta 5.82 (m, CH2CHCH2O, 1H), 5.23 (m, CH2CHCH2O, 1H), 5.01 (m, CH2CHCH2O, 1H), 3.82 (m, CH2CHCH2O, 2H), 3.50-3.43 (m, CH2, 12H), 3.42-3.40 (m, CH2, 2H), 3.34 (m, CH2, 2H), 3.12 (s, OCH3, 3H). 13C{1H} NMR (150 MHz, C6D6): 135.7, 115.9, 72.4, 72.1, 71.07, 71.04 (3), 71.0, 70.9, 70.0, 58.6. HRMS (ESI): m/z calcd for [C12H24O5Na]+ (M+Na): 271.1516; found 271.1506.

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, and friends who are interested can also refer to it.

Reference:
Article; Inomata, Koya; Naganawa, Yuki; Guo, Haiqing; Sato, Kazuhiko; Nakajima, Yumiko; Tetrahedron Letters; vol. 60; 41; (2019);,
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Adding a certain compound to certain chemical reactions, such as: 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, 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, Computed Properties of C9H20O5, blongs to alcohols-buliding-blocks compound. Computed Properties of C9H20O5

Synthesis of 2,5,8,11-tetraoxatridecan-13-ol Tosylate Procedure: (JACS, 2007, 129, 13364) To a solution of 2,5,8,11-tetraoxatridecan-13-ol (7 g, 33.6 mmol) and triethylamine (4.9 ml, 35.3 mmol) in dry CH2Cl2 (100 ml), 4-toluenesulfonyl chloride (6.7 g, 35.3 mmol) and DMAP (120 mg) were added. The mixture was stirred at room temperature for 20 h. The reaction mixture was washed with 80 mL of HCl (1M) and then water. The extract was dried over anhydrous MgSO4, filtrated, and the filtrate was evaporated. The residue was used in the next step without further purification. Yield: 11.0 g (90%) NMR: 1H NMR (400 MHz, CDCl3) delta 7.75-7.64 (m, 2H), 7.31-7.26 (m, 2H), 4.16-4.06 (m, 2H), 3.62 (m 2H), 3.59-3.40 (m, 10H), 3.30 (s, 3H), 2.38 (s, 3H). 13C{1H} NMR (101 MHz, CDCl3) delta 144.75 (s), 132.90 (s), 129.77 (s), 127.8 (s), 71.82 (s), 70.60 (s), 70.48 (s), 70.47 (s), 70.41 (s), 70.39 (s), 69.23 (s), 68.55 (s), 58.90 (s), 21.53 (s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, and friends who are interested can also refer to it.

Reference:
Patent; Bergmann, Frank; Cysewski, Robert; de Cola, Luisa; Dziadek, Sebastian; Fernandez Hernandez, Jesus Miguel; Josel, Hans-Peter; Seidel, Christoph; US2015/147750; (2015); A1;,
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Synthetic Route of 23783-42-8, 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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. A new synthetic method of this compound is introduced below.

Synthesis of 2,5,8,11-tetraoxatridecan-13-ol tosylate Procedure: [0187] (JACS, 2007, 129, 13364) To a solution of 2,5,8,11-tetraoxatridecan-13-ol (7 g, 33.6 mmol) and triethylamine (4.9 ml, 35.3 mmol) in dry CH2Cl2 (100 ml), 4-toluenesulfonyl chloride (6.7 g, 35.3 mmol) and DMAP (120 mg) were added. The mixture was stirred at room temperature for 20 h. The reaction mixture was washed with 80 mL of HCl (1M) and then water. The extract was dried over anhydrous MgSO4, filtrated, and the filtrate was evaporated. The residue was used in the next step without further purification. Yield: [0188] 11.0 g (90%) NMR: [0189] 1H NMR (400 MHz, CDCl3) delta 7.75-7.64 (m, 2H), 7.31-7.26 (m, 2H), 4.16-4.06 (m, 2H), 3.62 (m 2H), 3.59-3.40 (m, 10H), 3.30 (s, 3H), 2.38 (s, 3H). [0190] 13C{1H} NMR (101 MHz, CDCl3) delta 144.75 (s), 132.90 (s), 129.77 (s), 127.8 (s), 71.82 (s), 70.60 (s), 70.48 (s), 70.47 (s), 70.41 (s), 70.39 (s), 69.23 (s), 68.55 (s), 58.90 (s), 21.53 (s).

At the same time, in my other blogs, there are other synthetic methods of this type of compound,23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol, and friends who are interested can also refer to it.

Reference:
Patent; Bergmann, Frank; Cysewski, Robert; de Cola, Luisa; Dziadek, Sebastian; Fernandez Hernandez, Jesus Miguel; Josel, Hans-Peter; Seidel, Christoph; US2015/147751; (2015); A1;,
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Reference of 23783-42-8, 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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, 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.

An oven-dried 100 mL round bottom flask was charged with t-BuOK (13 mmol), dry THF (30 mL), purged with argon and cooled to 0C in an ice bath. Tetraethyleneglycol monomethyl ether (10 mmol) was then added dropwise to the solution and the reaction stirred at 0C for 1 h under argon. Allyl bromide (13 mmol) was added dropwise, and the solution was warmed to R.T. and allowed to stir for 24 h under argon. Deionized water (2 mL) was then added and the reaction stirred for 10 min. All liquid were then removed in vacuo and the residue redissolved in ethyl acetate (50 mL). The organic was washed three times with water (20 mL), dried over Na2S04, filtered over Celite and then concentrated in vacuo to yield clear/light yellow oil (47%). iHNMR (400 MHz, CDCb): delta = 5.90 (m, 1H), 5.23 (dd, 1H, 3jHHtram = 17.3 Hz, , 2jHHgem = 1.7 Hz), 5.15 (dd, 1H, 3JHH = 10.4 Hz, , iJHHgem = 1.5 Hz), 4.00 (dd, 2H, SJHH = 5.89 Hz, , 4JHH = 1.5 Hz), 3.65 (m, 12H), 3.59 (m, 2H), 3.53 (m, 2H), 3.36 (s 3H) ppm. isCNMR (400 MHz, CDCb): delta =134.8, 117.0, 72.2, 71.9, 70.6, 70.6, 70.6, 70.5, 69.4, 59.0 ppm. HRMS-ESI: Calculated [M+Na]+: 271.1516; found: 271.1516.

According to the analysis of related databases, 23783-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; THE REGENTS OF THE UNIVERSITY OF CALIFORNIA; GARRELL, Robin L.; TUCKER-SCHWARTZ, Alexander K.; WO2012/129380; (2012); A2;,
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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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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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol. A new synthetic method of this compound is introduced below., Safety of 2,5,8,11-Tetraoxatridecan-13-ol

Example 3. Allyl 2,2-bis(2,5,8,11,14-pentaoxadodecyl)-4,7,10,13,16-pentaoxatetradecyl ether (compound 5 of Scheme 1 wherein n=4) Tetraethyleneglycol monomethyl ether (1.91 ml, 9 mmol) dissolved in dry and degassed DMF (3.5 ml) was carefully added to sodium hydride (365 mg, 9 mmol) in dry and degassed DMF (15 ml) under nitrogen at 0 C using a syringe. The temperature was then raised to room temperature and the reaction mixture was stirred for another 30 min. Tribromide 4 (730 mg, 2.0 mmol, example 1) was then added and the temperature was raised to 100 C, After 14 h the reaction was completed and the temperature was decreased to room temperature whereupon the reaction mixture was slowly added to H2O (150 ml). The H2O-phase was washed with diethyl ether (2 x 50 ml). Sodium chloride was then added to the H2O-phase until saturation. The H2O-phase was extracted with EtOAc (4 x 50 ml) and the combined organic phases were washed with brine (2 x 30 ml). Sodium sulfate and charcoal was added to the organic phase. The clear organic phase was filtered and the volatile material was removed at reduced pressure. Column chromatography (EtOAc:MeOH 9:1) gave 1.05 g of the product. 1H-NMR (CDCl3); 5.90 (m, 1H), 5.20 (m, 2H), 3.94 (dt, 2H), 3.70-3.55 (m, 48H), 3.45 (s, 6H), 3.43 (s, 2H), 3.40 (s, 9H).

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, 23783-42-8, 2,5,8,11-Tetraoxatridecan-13-ol.

Reference:
Patent; Spago Imaging AB; Axelsson, Oskar; Ek, Fredrik; EP2573089; (2013); A1;,
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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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, 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. Computed Properties of C9H20O5

O-Tosyltetraethyleneglycol Methyl Ether (109) Tetraethyleneglycol monomethyl ether (2.0 g, 9.6 mmol) was combined with pyridine (0.93 mL, 11.5 mmol) in methylene chloride (20 mL) at 0 C. p-Toluenesulfonyl chloride (2.2 g, 11.5 mimol) dissolved in methylene chloride (10 mL) was added dropwise and the reaction was allowed to warm to room temperature as the ice bath thawed. After stirring nine days, the product mixture was transferred to a separatory funnel with water (70 mL). The layers were separated and the aqueous layer was extracted with methylene chloride (3*20 mL). The extracts were combined and evaporated. The residue (3.3 g) was chromatographed (silica gel, 4:1 to 3:1 gradient elution, methylene chloride/ethyl acetate) to afford 2.5 g (70%) of compound 109 as an oil. 1H NMR (300 MHz, DMSO-d6) delta 1.56 (br s, 411), 2.42 (br s, 2H), 3.34 (br s, 4H), 6.05 (s, 3H), 7.09 (s, 0.5H), 7.26 (s, 0.5H), 7.42 (br s, 2H), 7.70 (br s, 2H), 8.87 (br d, 2H), 9.07 (s, 2H), 9.22 (br s, 1H), 10.51 (s, 1H). CI MS m/z=363 [C16H26O7S+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 23783-42-8.

Reference:
Patent; CYFI, INC.; US2003/199456; (2003); A1;,
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Electric Literature of 23783-42-8, 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. 23783-42-8, name is 2,5,8,11-Tetraoxatridecan-13-ol, molecular formula is C9H20O5, 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.

To a stirred solution of 5-2A (180 mg, 0.87 mmol) in DCM (5 mL) was added triethylamine (0.18 mL, 1.3 mmol) and methane sulfonyl chloride (0.1 mL, 1.13 mmol) at 0 C and stirred at RT for 1 hr. The reaction mixture was diluted with excess DCM (40 mL) and washed with water (2 X 10 mL), brine (10 mL) and dried over Na2S04, organic phase concentrated under reduced pressure to get crude compound. This was purified using 100-200 silica gel column chromatography using 2% MeOH in DCM to afford 5-3A (200 mg, 0.699 mmol, 80% yield) as a yellow liquid.

According to the analysis of related databases, 23783-42-8, the application of this compound in the production field has become more and more popular.

Reference:
Patent; COCRYSTAL PHARMA, INC.; JACOBSON, Irina C.; FEESE, Michael D.; LEE, Sam S.; (169 pag.)WO2016/154241; (2016); A1;,
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