Category: 2050-25-1

Application of 2050-25-1, 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. 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

26.3 g of diethylene glycol benzyl ether was dissolved in 140 mL of DMF, 5.4 g of 60% NaH was added at 0 to 5 C., and the mixture was stirred for 30 minutes. Then, a solution of 17.3 g of 3-nitrophthalonitrile in 60 mL of DMF was added dropwise and the mixture was stirred at 0 to 5 C. for 2 hours. The reaction solution was discharged into 2500 mL of diluted hydrochloric acid, stirred for 30 minutes, and the precipitate was collected by filtration, washed with water and dried. The obtained solid was recrystallized from 80% isopropyl alcohol aqueous solution to obtain a yellowish white solid 21.7 g (melting point 98.5 to 100.5 C) was obtained.

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; YAMAMOTO CHEMICALS INCORPORATED; KUMAGAE, YOJIRO; HORIUCHI, KENICHIRO; (40 pag.)JP2016/204536; (2016); A;,
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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. 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, the common compound, a new synthetic route is introduced below. Recommanded Product: 2-(2-(Benzyloxy)ethoxy)ethanol

Sodium hydride (4.08 g, 102 mmol) was added portionwise to an ice bath-cooled solution of 2-(2-(benzy- loxy)ethoxy)ethanol (9.14 mE, 51.0 mmol) in THF (200 mE) over 15 minutes. The reaction was stirred for 1 h after which time tert-butyl 2-bromoacetate (8.97 mE, 61.1 mmol) in THF (50 mE) was added dropwise over 1 h. The reaction was stirred at ice bath temperature for 3 hand quenched with ammonium chloride (50 mE). TBME (250 mE) was added and the organic layer washed with brine (2×200 mE). The organic layer was concentrated onto silica and the crude product was purified by chromatography on silica gel (220g column, 0-50% EtOAc/isohexane) to afford the sub-titlecompound (1.95 g) as a colourless oil. ?H NMR (400 MHz, DMSO-d6) oe 7.43-7.20 (m,5H), 4.50 (s, 2H), 3.99 (s, 2H), 3.66-3.47 (m, 8H), 1.42 (s,9H)

The synthetic route of 2050-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Respivert Limited; Topivert Pharma Limited; FYFE, Matthew Colin Thor; THOM, Stephen Malcolm; (88 pag.)US2017/291917; (2017); A1;,
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Synthetic Route of 2050-25-1, Adding some certain compound to certain chemical reactions, such as: 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol,molecular formula is C11H16O3, 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 2050-25-1.

tert-Butyl 2 – (2 – (2 – (benzyloxy) ethoxy) ethoxy) acetate KOtBu (20 mL, 20 mmol) was added to a stirred solution of 2-(2-(benzyloxy)ethoxy)ethanol (commercially available from for example Aldrich) (2.74 mL, 15 mmol) in tBuOH (30 mL) and the mixture was stirred under a nitrogen atmosphere at room temperature for 2 hours. The reaction mixture was cooled to 0C, tert-butyl 2-bromoacetate (commercially available from for example Aldrich) (4 mL, 28 mmol) was added and the mixture stirred at room temperature overnight. The reaction mixture was then concentrated, and partitioned between water (50 mL) and DCM (50 mL). The organic layer was separated and the aqueous layer was extracted further with DCM (50 mL). The combined organic layers were 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 (3.56 g, 11 mmol, 74% yield). LCMS RT= 1.11 min, ES+ve m/z 311.4 [M+H]+, 328.4 [M+NH4] +.

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; GLAXOSMITHKLINE INTELLECTUAL PROPERTY DEVELOPMENT LIMITED; CAMPOS, Sebastien, Andre; HARLING, John, David; MIAH, Afjal, Hussain; SMITH, Ian, Edward, David; WO2015/867; (2015); A1;,
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Application of 2050-25-1 , The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

2-(2-(Benzyloxy)ethoxy)ethanol (5 g, 25.5 mmol) was dissolved in DCM (50 mE), passed through a phase separator and concentrated in vacuo. It was then redissolved in dry THF (50 mE, 25.5 mmol) under nitrogen and cooled in an ice bath. NaH (60% in mineral oil, 1.070 g, 26.8 mmol)was added portionwise over 10 mm and the resulting suspension stirred for 30 mm. Ethyl 2-bromopropanoate (3.73 mE, 28.0 mmol) was added dropwise over 15 mm. The reaction was stirred overnight, quenched with sat. NHa4C (5 mE) and the resulting mixture concentrated directly onto silica gel. The crude product was purified by chromatography on silica gel (80 g column, 0-50% EtOAc/isohexane) to afford the sub-title compound (1.51 g) as a colourless oil.?H NMR (400 MHz, DMSO-d6) oe 7.51-7.09 (m, 5H), 4.50 (s, 2H), 4.11 (qd, 2H), 4.05 (q, 1H), 3.70-3.41 (m, 8H), 1.27 (d, 3H), 1.20 (t, 3H)

The synthetic route of 2050-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; Respivert Limited; Topivert Pharma Limited; FYFE, Matthew Colin Thor; THOM, Stephen Malcolm; (88 pag.)US2017/291917; (2017); A1;,
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Reference of 2050-25-1, 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. 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

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.

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

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;,
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2050-25-1 , The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

Step (i): 2-(2-(Benzyloxy)ethoxy)ethyl methanesulfonate (47) MsCI (15.8 mL. 204 mmol) was added to a solution of 2-(2-(benzyloxy)ethoxy)ethanol (46) (25 g, 127 mmol) and Et3N (36 mL, 255 mmol) in DCM (180 mL) at 0C, the reaction mixture was allowed to warm up to RT and stirred for 16h. The reaction mixture was diluted with DCM (50 mL) and washed with water (2 x 50 mL), 1 M HCI (aq.) (2 x 50 mL), the organic layer was dried (MgS04), filtered and concentrated in vacuo to afford 2-(2-(benzyloxy)ethoxy)ethyl methanesulfonate (47) (35 g, 100 %) as an orange oil: m/z 275 (M+H)+ (ES+). 1 H NMR (400 MHz, CDCIs) delta: 7.37-7.27 (m, 5H), 4.55 (s, 2H), 4.40-4.37 (m, 2H), 3.78-3.76 (m, 2H), 3.71-3.68 (m, 2H), 3.64-3.62 (m, 2H), 3.02 (s, 3H).

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; UNIVERSITY OF LEICESTER; ANDREW, Peter William; LONNEN, Rana; DAMASO, Mafalda Pires; FRICKEL, Fritz-Frieder; HIRST, Simon Christopher; DAVIES, Mark William; HAMZA, Daniel; WO2013/83975; (2013); A2;,
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The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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. 2050-25-1

Step 1. 2-(2-(2-(Benzyloxy)ethoxy)ethoxy)acetonitrile. To a stirring solution of diethylene glycol benzyl ether (1.0 g, 5.1 mmol) in THF (10 mL) at 0 C, was added in small portions NaH (408 mg, 10.2 mmol), then the reaction mixture was warmed to rt and stirred for 30 mins. The reaction mixture was cooled to 0 C, and bromoacetonitrile (0.39 mL, 5.6 mmol) was added dropwise and stirred for 3h. The reaction was quenched with saturated ammonium chloride, and extracted with EtOAc (3 x 50 mL). The combined organic phase was washed with brine, dried over magnesium sulfate, filtered and concentrated. The crude residue was further purified by silica gel chromatography using 25% acetone/hexanes eluent to afford 2-(2-(2-(benzyloxy)ethoxy)ethoxy)acetonitrile as a colorless oil (437 mg, 37%): XH NMR (500MHz, CDC13) delta ppm 7.35 (d, J= 4.9 Hz, 4H), 7.27 – 7.32 (m, 1H), 4.57 (s, 2H), 4.33 (s, 2H), 3.76 – 3.80 (m, 2H), 3.67 – 3.74 (m, 4H), 3.62 – 3.66 (m, 2H).

The synthetic route of 2050-25-1 has been constantly updated, and we look forward to future research findings.

Reference:
Patent; NORTHEASTERN UNIVERSITY; MALAMAS, Michael; MAKRIYANNIS, Alexandros; SUBRAMANIAN, Kumara Vadivel; WHITTEN, Kyle M.; ZVONOK, Nikolai M.; WEST, Jay Matthew; MCCORMACK, Michael; PAVLOPOULOS, Spiro; WO2015/179190; (2015); A1;,
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2050-25-1, 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. 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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-(2-Benzyloxyethoxy)ethanol [44] (1, 12.96 g, 66 mmol) and succinic acid anhydride (8.12 g, 81.1 mmol) were dissolved in CH2Cl2 (200 ml), and DMAP (9.95 g, 81.4 mmol) was added. The solution was stirred at ambient temperature for 1 h. Then AcOH (1 ml) was added and the mixture was evaporated under reduced pressure. The crude product was purified by gradient Fc (toluene/AcOEt/AcOH 150:50:2 to 25:75:1). This provided an oily liquid. Yield: 10 g (51%). 1H NMR (250 MHz, CDCl3), delta: 2.64 (s, 4H, COCH2CH2CO), 3.60-3.72 (m, 6H, PhCH2OCH2CH2OCH2CH2), 4.22-4.30 (m, 2H, CH2CH2OCO), 4.57 (s, 2H, PhCH2O), 7.30-7.37 (m, 5H, Ph), 10.53 (s, 1H, COOH). 13C NMR (62.5 MHz, CDCl3), delta: 29.0, 29.0, 63.9, 69.1, 69.4, 70.6, 73.3, 127.7, 127.9, 128.4, 138.1, 172.2 (COOR), 177.3 (COOH).

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. 2050-25-1, 2-(2-(Benzyloxy)ethoxy)ethanol, other downstream synthetic routes, hurry up and to see.

Reference:
Article; Coufalova, Lenka; Mrozek, Lech; Rarova, Lucie; Pla?ek, Luka?; Opat?ilova, Radka; Dohnal, Ji?i; Kral’Ova, Katarina; Paleta, Old?ich; Kral, Vladimir; Dra?ar, Pavel; Jampilek, Josef; Steroids; vol. 78; 5; (2013); p. 435 – 453;,
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2050-25-1 , The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

Under a nitrogen atmosphere, silver trifluoromethane sulfonate (19.64 g, 76.44 mmol), lithium trifluoromethane sulfonate (3.97 g, 25.48 mmol), 1-(chloromethyl)-4-fluoro- 1,4-diazoniabicyclo[2.2.2]octane bis(tetrafluoroborate) (18.05 g, 50.96 mmol) and potassium fluoride (5.92 g, 101.92 mmol) were mixed.2-(2-benzyloxyethoxy)ethanol (5 g, 25.48 mmol), trimethyl(1,1,2,2,2-pentafluoroethyl)silane (14.69 g, 76.44 mmol), EtOAc (20 mL), trifluoromethylbenzene (20 mL), and 2-fluoropyridine (7.42 g, 76.44 mmol) were then added under N2 atmosphere in this order. The reaction mixture was stirred under N2 atmosphere for 60 h at 30 C then filtered through a plug of silica (eluting with EtOAc). The filtrate was collected and concentrated. The residue was purified via silica gel chromatography (PE:EtOAc = 25:1) to obtain 2-[2-(1,1,2,2,2-pentafluoroethoxy)ethoxy]ethoxymethylbenzene (2.5 g, 31% yield) as a light yellow liquid. 1H NMR (400 MHz, CDCl3) d 7.36- 7.24 (m, 5H), 4.56 (s, 2H), 4.17- 4.11 (m, 2H), 3.76- 3.72 (m, 2H), 3.71- 3.65 (m, 2H), 3.65- 3.60 (m, 2H). 19F NMR (376 MHz, CDCl3) d -90.77 (s), -86.02 (s).

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; NAVITOR PHARMACEUTICALS, INC.; SAIAH, Eddine; O’NEILL, David, John; KANG, Seong Woo Anthony; (366 pag.)WO2019/241789; (2019); A1;,
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2050-25-1 , The common heterocyclic compound, 2050-25-1, name is 2-(2-(Benzyloxy)ethoxy)ethanol, molecular formula is C11H16O3, 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.

To a suspension of sodium hydride, 60% w/w in mineral oil (0.92 g, 22.9 mmol) in DMF (5 mL) was added a solution of 2-(2-(benzyloxy)ethoxy)ethanol (commercially available from for example Aldrich) (2.74 mL, 15.29 mmol) in DMF (5 mL) at 0 C. After stirring for 25 min, 1,4-dibromobutane (commercially available from for example Aldrich) (14.9 g, 68.8 mmol) dissolved in DMF (5 mL) was added dropwise to the mixture. The reaction was warmed to ambient temperature and stirred under an atmosphere of nitrogen for 2.5 hours. A further aliquot of sodium hydride, 60% w/w in mineral oil (0.92 g, 22.9 mmol) was added and the reaction was stirred at 0 C. for 30 minutes and at ambient temperature for 30 minutes. A final aliquot of sodium hydride, 60% w/w in mineral oil (0.92 g, 22.9 mmol) was added and the reaction stirred at ambient temperature for 2 hours then left standing overnight. 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¡Á30 mL), dried using a hydrophobic frit, and concentrated under reduced pressure. The product was purified by chromatography on silica using a using a gradient elution from 0% to 80% methyl tert-butyl ether in cyclohexane to afford the title compound (3 g, 9.06 mmol, 59% yield). LCMS RT=1.19 min, ES+ve m/z 331.2/333.2 [M+H]+.

According to the analysis of related databases, 2050-25-1, the application of this compound in the production field has become more and more popular.

Reference:
Patent; Crews, Craig M.; Buckley, Dennis; Ciulli, Alessio; Jorgensen, William; Gareiss, Peter C.; Van Molle, Inge; Gustafson, Jeffrey; Tae, Hyun-Seop; Michel, Julien; Hoyer, Dentin Wade; Roth, Anke G.; Harling, John David; Smith, Ian Edward David; Miah, Afjal Hussain; Campos, Sebastien Andre; Le, Joelle; US2014/356322; (2014); A1;,
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