Category: 55489-58-2

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. 55489-58-2, name is 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol, molecular formula is C13H20O4, 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. category: alcohols-buliding-blocks

General procedure: Methanesulfonyl chloride (1.5 equiv.) was added drop-wise to astirred solution of alcohol (1 equiv.) and Et3N (1.5 equiv.) in anhydrousDCM (30 mL) at 0 C under nitrogen. The reaction wasallowed to warm to room temperature, and stirred for 2 h. Thereaction mixture was poured into methanol (10 mL), and concentratedin vacuo. The reaction mixture was then diluted with diethylether (20 mL), washed with water (3 20 mL) and brine(3 20 mL). The combined organic extracts were then dried overanhydrous MgSO4, filtered, and concentrated in vacuo. The residuewas dissolved in DMF (25 mL), sodium azide (3 equiv.) was added, and the mixture was stirred at 60 C for 16 h. The reaction mixturewas concentrated in vacuo, and The reaction mixture was thendiluted with diethyl ether (50 mL), washed with water (3 20 mL)and brine (3 30 mL), dried over anhydrous MgSO4, filtered, andconcentrated in vacuo, to give a residue which was purified by flashchromatography.

With the rapid development of chemical substances, we look forward to future research findings about 55489-58-2.

Reference:
Article; Suthagar, Kajitha; Watson, Andrew J.A.; Wilkinson, Brendan L.; Fairbanks, Antony J.; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 153 – 166;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 55489-58-2, name is 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol, the common compound, a new synthetic route is introduced below. category: alcohols-buliding-blocks

15-Bromo-1-phenyl-2,5,8,11-tetraoxapentadecane To a suspension of sodium hydride, 60% w/w in mineral oil (0.250 g, 6.24 mmol) in DMF (2 mL) was added a solution of 2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethanol (1 g, 4.16 mmol) (Fluorochem) in DMF (2 mL) at 0 C. After stirring for 25 minutes, 1,4-dibromobutane (Aldrich) (4.04 g, 18.73 mmol) dissolved in DMF (2 mL) was added dropwise to the mixture. The reaction was stirred under an atmosphere of nitrogen for 2.5 hours. A further aliquot of sodium hydride, 60% w/w in mineral oil (0.250 g, 6.24 mmol) was added and the reaction was stirred at 0 C. for 30 minutes. The reaction was warmed to room temperature and stirred for 30 minutes. A final aliquot of sodium hydride, 60% w/w in mineral oil (0.250 g, 6.24 mmol), was added and the reaction stirred at room temperature for 2 hours then left standing over the weekend. The reaction mixture was filtered through celite and the solid washed with DCM. The filtrate was partitioned between DCM (30 mL) and water (30 mL). The organic extract was washed with brine (2*30 mL), dried using a hydrophobic frit and concentrated under reduced pressure. The product was purified by chromatography on silica using a gradient elution from 0% to 100% methyl tert-butyl ether in cyclohexane to afford the title compound (711 mg, 1.89 mmol, 46% yield). LCMS RT=1.16 min, ES+ve m/z 375.2/377.1 [M+H]+.

The synthetic route of 55489-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Yale University; Arvinas, Inc.; Crew, Andrew; Crews, Craig; Dong, Hanqing; Ko, Eunhwa; Wang, Jing; (89 pag.)US2016/45607; (2016); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 55489-58-2, name is 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol, molecular formula is C13H20O4, 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. HPLC of Formula: C13H20O4

15-Bromo-1 -phenyl-2,5,8,11-tetraoxapentadecane To a suspension of sodium hydride, 60 % w/w in mineral oil (0.250 g, 6.24 mmol) in DMF (2 mL) was added a solution of 2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethanol (1 g, 4.16 mmol) (commercially available from for example Fluorochem) in DMF (2 mL) at 0 C. After stirring for 25 minutes, 1,4-dibromobutane (commercially available from for example Aldrich) (4.04 g, 18.73 mmol) dissolved in DMF (2 mL) was added dropwise to the mixture. The reaction was stirred under an atmosphere of nitrogen for 2.5 hours. A further aliquot of sodium hydride, 60 % w/w in mineral oil (0.250 g, 6.24 mmol) was added and the reaction was stirred at 0 C for 30 minutes. The reaction was warmed to room temperature and stirred for 30 minutes. A final aliquot of sodium hydride, 60 % w/w in mineral oil (0.250 g, 6.24 mmol) was added and the reaction stirred at room temperature for 2 hours then left standing over the weekend. The reaction mixture was filtered through celite and the solid washed with DCM. The filtrate was partitioned between DCM (30 mL) and water (30 mL). The organic extract was washed with brine (2 x 30 mL), dried using a hydrophobic frit and concentrated under reduced pressure. The product was purified by chromatography on silica using a gradient elution from 0% to 100% methyl tert-butyl ether in cyclohexane to afford the title compound (711 mg, 1.89 mmol, 46% yield). LCMS RT= 1.16 min, ES+ve m/z 375.2/377.1 [M+H]+.

With the rapid development of chemical substances, we look forward to future research findings about 55489-58-2.

Reference:
Patent; YALE UNIVERSITY; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMBRIDGE ENTERPRISE LIMITED UNIVERSITY OF CAMBRIDGE; CREWS, Craig, M.; BUCKLEY, Dennis; CIULLI, Alessio; JORGENSEN, William; GAREISS, Peter, C.; MOLLE, Inge, Van; GUSTAFSON, Jeffrey; TAE, Hyun-Seop; MICHEL, Julien; HOYER, Dentin, Wade; ROTH, Anke, G.; HARLING, John, David; SMITH, Ian Edward, David; MIAH, Afjal, Hussain; CAMPOS, Sebastian, Andre; LE, Joelle; WO2013/106646; (2013); A2;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Application of 55489-58-2 ,Some common heterocyclic compound, 55489-58-2, molecular formula is C13H20O4, 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.

tert-But l l-phenyl-2,5,8,ll-tetraoxatridecan-13-oate Potassium tert-butoxide (commercially available from for example Aldrich) (7.71 g, 69 mmol) was added to a stirred solution of 2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethanol (commercially available from for example Fluorochem) (15 g, 62 mmol) in tert-butanol (200 mL) and the reaction mixture was stirred at room temperature for 2 h. The reaction mixture was cooled to 0C, tert-butyl 2- bromoacetate (commercially available from for example Aldrich) (17 mL, 112 mmol) was added, and the mixture was stirred at room temperature overnight. DCM (300 mL) was added ant the organic phase was washed with water (300 mL) and then brine (2 x 200 mL). The organic extract was dried using a hydrophobic frit and concentrated under reduced pressure to give the crude product as a yellow oil. The product was purified by chromatography on silica using a gradient elution from 0% to 100% methyl tert-butyl ether in cyclohexane to afford the title compound (13.3 g, 38 mmol, 60% yield). LCMS RT= 1.10 min, ES+ve m/z 372.4 [M+NH4]+.

These compound has a wide range of applications. It is believed that with the continuous development of the source of the synthetic route,55489-58-2, its application will become more common.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMPOS, Sebastien, Andre; HARLING, John, David; MIAH, Afjal, Hussain; SMITH, Ian, Edward, David; WO2015/867; (2015); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

Electric Literature of 55489-58-2, Adding some certain compound to certain chemical reactions, such as: 55489-58-2, name is 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol,molecular formula is C13H20O4, 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 55489-58-2.

A. Triethylene Glycol MonoBenzyl Tosyl Ether 4-Toluenesulfonyl chloride (20.9 g, 0.11 mol) was added to a cold (0 QC) solution of triethylene glycol monobenzyl ether (“BnO-3EG-OH, ” 24.0 g, 0.1 1 mol) in pyridine (100 mL) in portions over a period of two minutes. A precipitate formed over 20 minutes. After 70 minutes the reaction mixture was allowed to warm to room temperature overnight. After 16 hours the reaction was diluted with ethyl acetate (100 mL) and quenched with water (50 mL) to dissolve the solids. The layers were separated and the organic layer was washed with aqueous hydrochloric acid till the aqueous layer was about pH 1. The organic solution was dried over magnesium sulfate and concentrated to dryness to give the title compound (28.94 g). 1H NMR (400 MHz, CDCI3, A10899) indicated an ca 4: 1 mixture of desired triethylene glycol monobenzyl ether tosylate and undesired ({2-[2-(2-chloroethoxy)ethoxy]- ethoxy}methyl)benzene. Triethylene glycol monobenzyl ether tosylate: No.H (CDCl3, ppm from TMS) 7.79 (2 H, d, J= 8.3 Hz, Ar-H), 7.4-7.2 (7 H, m, Ar-H), 4.55 (2 H, s, PhCH20-), 4.15 (2 H, t, J= 4.7 Hz, CH2) 3.7-3.5 (10 H, m, CH2 x 5), 2.43 (3 H, s, ArCH3). ({2-[2-(2-Chloroethoxy) ethoxy]ethoxy)methyl)benzene: No.H (CDCI3, ppm from TMS) 7.4-7.2 (5 H, m, Ar-/@, 4.57 (2 H, s, PhCH20-), 3.76 (2 H, t, J= 5.9 Hz, CH2CI) 3.7- 3.5 (10 H, m, CH2 x 5). Mixture calculated to contain 88.4 wt% tosylate (25.58 g, 64.9% theory) and 11.6 wt% chloride (3.36 g, 13.0 % theory).

According to the analysis of related databases, 55489-58-2, the application of this compound in the production field has become more and more popular.

Reference:
Patent; SMITHKLINE BEECHAM CORPORATION; WO2005/102976; (2005); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 55489-58-2, name is 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol. This compound has unique chemical properties. The synthetic route is as follows. Formula: C13H20O4

General procedure: Methanesulfonyl chloride (1.5 equiv.) was added drop-wise to astirred solution of alcohol (1 equiv.) and Et3N (1.5 equiv.) in anhydrousDCM (30 mL) at 0 C under nitrogen. The reaction wasallowed to warm to room temperature, and stirred for 2 h. Thereaction mixture was poured into methanol (10 mL), and concentratedin vacuo. The reaction mixture was then diluted with diethylether (20 mL), washed with water (3 20 mL) and brine(3 20 mL). The combined organic extracts were then dried overanhydrous MgSO4, filtered, and concentrated in vacuo. The residuewas dissolved in DMF (25 mL), sodium azide (3 equiv.) was added, and the mixture was stirred at 60 C for 16 h. The reaction mixturewas concentrated in vacuo, and The reaction mixture was thendiluted with diethyl ether (50 mL), washed with water (3 20 mL)and brine (3 30 mL), dried over anhydrous MgSO4, filtered, andconcentrated in vacuo, to give a residue which was purified by flashchromatography.

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, 55489-58-2, 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol.

Reference:
Article; Suthagar, Kajitha; Watson, Andrew J.A.; Wilkinson, Brendan L.; Fairbanks, Antony J.; European Journal of Medicinal Chemistry; vol. 102; (2015); p. 153 – 166;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts

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. 55489-58-2, name is 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)ethanol, the common compound, a new synthetic route is introduced below. Formula: C13H20O4

2-(2-(2-(benzyloxy)ethoxy)ethoxy)ethanol (1.0 g, 4.16 mmol) and carbon tetrabromide (1.40 g, 4.2 mmol) were dissolved in dichloromethane under an argon atmosphere. The flask was placed in a water bath and triphenylphosphine (1.10 g, 4.2 mmol) in dichloromethane (10 ml_) was added drop-wise over 15 minutes. After stirring for an additional 2 hours at room temperature, the solution was concentrated and the product was purified by flash column chromatography on silica gel (30 g), eluting with a mixture of heptanes/ethyl acetate (3:1 ). The experiment generated ((2-(2-(2- bromoethoxy)ethoxy)ethoxy)methyl)benzene 5 (1 .0 g, 80% yield) as a colorless liquid. 1H NMR (300 MHz, CDCI3): 7.60-7.40 (m, 5H), 4.56 (s, 2H), 3.79 (t, 2H, J = 6.3 Hz), 3.72-3.55 (m, 8H), 3.44 (t, 2H, J = 6.3 Hz). 13C (75 MHz, CDCI3): 138.24, 128.37, 127.74, 127.61 , 73.34, 71.32, 70.83, 70.76, 70.66, 69.55, 30.55.

The synthetic route of 55489-58-2 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; RODOS BIOTARGET GMBH; AUGUSTUS BIOTARGET, INC.; SCOLARO, Michael, J.; SULLIVAN, Sean, M.; GIESELER, Robert, K.; HOZSA, Constantin; FURCH, Marcus; (68 pag.)WO2017/17148; (2017); A1;,
Alcohol – Wikipedia,
Alcohols – Chemistry LibreTexts