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Quality Control of [ 50586-80-6 ]

COA NMR CNMR HPLC LC-MS

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Product Details of [ 50586-80-6 ]

CAS No. :	50586-80-6	MDL No. :	MFCD13184964
Formula :	C₁₂H₁₈O₅S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	PBKGNJXLJQARIN-UHFFFAOYSA-N
M.W :	274.33	Pubchem ID :	11076628
Synonyms :		Chemical Name :	2-(2-Methoxyethoxy)ethyl 4-methylbenzenesulfonate

Safety of [ 50586-80-6 ]

Signal Word:	Warning	Class:	N/A
Precautionary Statements:	P261-P305+P351+P338	UN#:	N/A
Hazard Statements:	H302-H315-H319-H335	Packing Group:	N/A
GHS Pictogram:

Application In Synthesis of [ 50586-80-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 50586-80-6 ]
Downstream synthetic route of [ 50586-80-6 ]

[ 50586-80-6 ] Synthesis Path-Upstream 1~4

1
[ 50586-80-6 ]
[ 123-91-1 ]
[ 67-56-1 ]
[ 111-77-3 ]

Reference： [1] Journal of Organic Chemistry, 1988, vol. 53, # 3, p. 681 - 683

2
[ 112-60-7 ]
[ 50586-80-6 ]
[ 23601-40-3 ]

Reference： [1] Journal of the Chemical Society - Perkin Transactions 1, 1997, # 9, p. 1357 - 1360

3
[ 50586-80-6 ]
[ 54149-17-6 ]

Reference： [1] Journal of Organic Chemistry, 2008, vol. 73, # 5, p. 1787 - 1794
[2] Tetrahedron Letters, 2007, vol. 48, # 28, p. 4813 - 4815
[3] Patent: US2009/187037, 2009, A1, . Location in patent: Page/Page column 2-3
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1381 - 1384

4
[ 50586-80-6 ]
[ 31576-51-9 ]

Reference： [1] European Journal of Organic Chemistry, 2010, # 21, p. 3991 - 4003
[2] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1381 - 1384
[3] Journal of the American Oil Chemists' Society, 1996, vol. 73, # 1, p. 79 - 86
[4] Journal of the American Chemical Society, 1994, vol. 116, # 12, p. 5057 - 5062
[5] Journal of Organic Chemistry, 2011, vol. 76, # 6, p. 1683 - 1691
[6] Angewandte Chemie - International Edition, 2012, vol. 51, # 5, p. 1152 - 1155
[7] Patent: EP2439204, 2012, A1,
[8] Macromolecules, 2012, vol. 45, # 3, p. 1362 - 1374
[9] Macromolecules, 2012, vol. 45, # 12, p. 5151 - 5156
[10] Inorganica Chimica Acta, 2016, vol. 452, p. 159 - 169

[ 50586-80-6 ] Synthesis Path-Downstream 1~43

1
[ 2425-41-4 ]
[ 50586-80-6 ]
[ 87104-88-9 ]

Reference： [1]Liebigs Annalen der Chemie,1983,p. 770 - 801

2
[ 106-41-2 ]
[ 50586-80-6 ]
[ 112968-89-5 ]

Reference： [1]Tetrahedron Letters,2016,vol. 57,p. 959 - 963
[2]Analytical Chemistry,1988,vol. 60,p. 901 - 905

3
[ 50586-80-6 ]
[ 41775-76-2 ]
[ 98269-19-3 ]

Yield	Reaction Conditions	Operation in experiment
66%	With sodium carbonate In acetonitrile for 20h; Heating;

Reference： [1]Arnold, Kristin A.; Mallen, Jesus; Trafton, John E.; White, Banita D.; Fronczek, Frank R.; et al. [Journal of Organic Chemistry, 1988, vol. 53, # 24, p. 5652 - 5657]

4
[ 50586-80-6 ]
[ 111853-53-3 ]
[ 148561-02-8 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydride 1) DMF, r.t., 30 min., 2) DMF, r.t., 24 h; Yield given. Multistep reaction;

Reference： [1]Echegoyen, L.; Martinez-Diaz, M. V.; Mendoza, J. de; Torres, T.; Vicente-Arana, M. J. [Tetrahedron, 1992, vol. 48, # 43, p. 9545 - 9552]

5
[ 50586-80-6 ]
[ 104539-21-1 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium iodide; In acetone; at 60℃; for 48h;	To 25 g of the above-mentioned synthesis of diethylene glycol monomethyl ether paratoluene sulfonyl compound is dissolved in 30 ml in acetone, while stirring slowly adding 15 g sodium iodide solid, 60 C the reflux condensation of the reaction 48 h. After the reacting liquid to return to room temperature, 40 C steaming and drying to remove a large amount of acetone, then 120 C steaming and drying 24 h, to get the two ethylene glycol monomethyl ether iodide.

Reference： [1]Chemistry of Materials,2012,vol. 24,p. 1583 - 1590
[2]Inorganic Chemistry,2020
[3]Journal of Medicinal Chemistry,1991,vol. 34,p. 1805 - 1818
[4]Journal of Heterocyclic Chemistry,2012,vol. 49,p. 652 - 657
[5]Tetrahedron Letters,2007,vol. 48,p. 4813 - 4815
[6]Patent: US2009/187037,2009,A1 .Location in patent: Page/Page column 2-3
[7]Angewandte Chemie - International Edition,2004,vol. 43,p. 1718 - 1721
[8]Pharmaceutica Acta Helvetiae,1998,vol. 73,p. 3 - 10
[9]Dalton Transactions,2013,vol. 42,p. 2062 - 2074
[10]Patent: CN108218782,2018,A .Location in patent: Paragraph 0050; 0052

6
[ 50586-80-6 ]
[ 66943-05-3 ]
[ 79402-96-3 ]

Reference： [1]Chemische Berichte,1984,vol. 117,p. 234 - 245

7
[ 55515-99-6 ]
[ 50586-80-6 ]
[ 71776-34-6 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide

Reference： [1]Helgeson,R.C. et al. [Journal of the American Chemical Society, 1979, vol. 101, # 17, p. 4928 - 4941]

8
[ 1506-76-9 ]
[ 50586-80-6 ]
[ 63239-73-6 ]

Reference： [1]Journal of Organic Chemistry,1978,vol. 43,p. 1808 - 1811

9
[ 50586-80-6 ]
[ 88778-21-6 ]

Yield	Reaction Conditions	Operation in experiment
91%	Stage #1: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester With thiourea In ethanol for 3h; Heating; Stage #2: With sodium hydroxide for 3.75h; Heating;
75%	Stage #1: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester With carbon disulfide; sodium trithiocarbonate at 65℃; for 5h; Stage #2: With sulfuric acid
	Stage #1: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester With thiourea In ethanol; water for 3h; Reflux; Stage #2: With sodium hydroxide for 1.5h; Reflux;

Reference： [1]Snow, Arthur W.; Foos, Edward E. [Synthesis, 2003, # 4, p. 509 - 512]
[2]Yanic, Cemile; Bredenkamp, Martin W.; Jacobs, Edmund P.; Swart, Pieter [Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 7, p. 1381 - 1384]
[3]Tsiamantas, Christos; Dawson, Simon J.; Huc, Ivan [Comptes Rendus Chimie, 2016, vol. 19, # 1-2, p. 132 - 142]

10
[ 6272-38-4 ]
[ 50586-80-6 ]
[ 535967-53-4 ]

Yield	Reaction Conditions	Operation in experiment
92%	With sodium hydroxide In 1,4-dioxane at 80℃; for 24h;

Reference： [1]Tsuda, Akihiko; Fukumoto, Chikako; Oshima, Takumi [Journal of the American Chemical Society, 2003, vol. 125, # 19, p. 5811 - 5822]

11
[ 50586-80-6 ]
[ 128143-88-4 ]
4'-[2-(1-methoxyethoxy)ethoxy]-2,2':6',2''-terpyridine [ No CAS ]

Reference： [1]Synthesis,2003,p. 2865 - 2871

12
[ 50586-80-6 ]
[ 95-12-5 ]
5-[2-(2-methoxyethoxy)ethoxymethyl]norbornene [ No CAS ]

Reference： [1]Macromolecules,2003,vol. 36,p. 3563 - 3569

13
[ 40501-41-5 ]
[ 50586-80-6 ]
[ 823222-06-6 ]

Reference： [1]Molecular Crystals and Liquid Crystals,2004,vol. 414,p. 27 - 38

14
[ 4877-80-9 ]
[ 50586-80-6 ]
2,3,6,7,10,11-hexa(2-(2-methoxyethoxy)ethoxy)triphenylene [ No CAS ]

Reference： [1]Chemistry - A European Journal,2005,vol. 11,p. 2519 - 2524

15
[ 50586-80-6 ]
[ 246232-73-5 ]
[ 919524-45-1 ]

Reference： [1]Bioorganic and Medicinal Chemistry,2007,vol. 15,p. 186 - 193
[2]Journal of Organic Chemistry,2012,vol. 77,p. 9641 - 9651

16
[ 50586-80-6 ]
[ 31576-51-9 ]

Reference： [1]European Journal of Organic Chemistry,2010,p. 3991 - 4003
[2]Bioorganic and Medicinal Chemistry Letters,2003,vol. 13,p. 1381 - 1384
[3]Journal of the American Oil Chemists' Society,1996,vol. 73,p. 79 - 86
[4]Journal of the American Chemical Society,1994,vol. 116,p. 5057 - 5062
[5]Journal of Organic Chemistry,2011,vol. 76,p. 1683 - 1691
[6]Angewandte Chemie - International Edition,2012,vol. 51,p. 1152 - 1155
[7]Patent: EP2439204,2012,A1
[8]Macromolecules,2012,vol. 45,p. 1362 - 1374
[9]Macromolecules,2012,vol. 45,p. 5151 - 5156
[10]Inorganica Chimica Acta,2016,vol. 452,p. 159 - 169

17
[ 50586-80-6 ]
[ 84478-72-8 ]
4-chloro-2-fluoro-5-(2-(2-methoxy-ethoxy)-ethoxy)-aniline [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide; In 1-methyl-pyrrolidin-2-one; dichloromethane; water;	STR545 20 g (0.124 mol) of <strong>[84478-72-8]4-chloro-2-fluoro-5-hydroxyaniline</strong> are dissolved in 140 ml of N-methylpyrrolidone, and 10.2 g (0.186 mol) of potassium hydroxide in 12 ml of water and also 35.6 g (0.130 mol) of 2-(2-methoxy-ethoxy)-ethyl p-toluenesulphonate are added in succession. The mixture is stirred at room temperature for 18 hours, and most of the solvent is then removed in vacuo. 200 ml of water are added to the oily residue, and the oil which separates is extracted using dichloromethane. The organic phase is separated off, washed, dried and concentrated in vacuo. As the residue, 30.5 g (93.3 % of theory) of 4-chloro-2-fluoro-5-[2-(2-methoxy-ethoxy)-ethoxy]-aniline remain as an oil. 1 H-NMR (CDCl3): delta=6.98 ppm (1H, d).

Reference： [1]Patent: US5039334,1991,A

18
[ 50586-80-6 ]
[ 84905-80-6 ]
[ 919278-13-0 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 12h;	Example 171 Production of N-{3-chloro-4-[3-(trifluoromethyl)phenoxy]phenyl}-5-[2-(2-methoxyethoxy)ethyl]-5H-pyrrolo[3,2-d]pyrimidin-4-amine hydrochloride <strong>[84905-80-6]4-Chloro-5H-pyrrolo[3,2-d]pyrimidine</strong> (500 mg) was dissolved in N,N-dimethylformamide (10 mL), and potassium carbonate (830 mg) and 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate (920 mg) were added and the mixture was stirred at room temperature for 12 hrs. Saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and concentrated. The residue was purified by silica gel column chromatography (eluent, hexane:ethyl acetate=50:50 ? 0:100). The obtained oil was dissolved in isopropyl alcohol (10 mL), and 3-chloro-4-[3-(trifluoromethyl)phenoxy]aniline was added. The mixture was stirred at 90C for 4 hrs, saturated aqueous sodium hydrogen carbonate was added to the reaction mixture under ice-cooling, and the mixture was extracted with ethyl acetate. The extract was dried over magnesium sulfate and concentrated. The residue was separated and purified by silica gel column chromatography (eluent, ethyl acetate:methanol=100:0 ? ethyl acetate:methanol=90:10), and crystallized from 4N hydrochloric acid-ethyl acetate solution/hexane to give the title compound (277 mg). 1H-NMR(DMSO-d6) delta: 3.06 (3H, s), 3.33 - 3.35 (2H, m), 3.55 - 3.61 (2H, m), 3.83 - 3.86 (2H, m), 4.83 - 4.86 (2H, m), 6.71 (1H, d, J= 3 Hz), 7.24 - 7.72 (7H, m), 7.99 - 8.04 (2H, m), 8.77 (1H, s), 9.92 (1H, s).

Reference： [1]Patent: EP1752457,2007,A1 .Location in patent: Page/Page column 204

19
[ 50586-80-6 ]
[ 13064-64-7 ]
[ 271790-35-3 ]

Reference： [1]Journal of the American Chemical Society,2007,vol. 129,p. 15911 - 15918

20
[ 99-24-1 ]
[ 50586-80-6 ]
[ 422267-94-5 ]

Yield	Reaction Conditions	Operation in experiment
92.3%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 48h; Inert atmosphere;
87%	With potassium carbonate; potassium iodide In N,N-dimethyl-formamide at 80℃; for 24h; Inert atmosphere;
70%	Stage #1: methyl galloate With potassium carbonate In 1,4-dioxane at 20℃; for 1h; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In 1,4-dioxane at 110℃; for 36h;	8.2 (2) Preparation of methyl 3,4,5-tris(2-(2-methoxyethoxy)ethoxy)benzoate Methyl gallate (8.89 g, 0.048 mοl) and anhydrous potassium carbonate were sequentially added to a 500 mL single-mouth bottle.(39.99g, 0.290mmol) and 220mL of 1,4-dioxane, stirred at room temperature for 1h, then added -(2-methoxyethoxy)ethyl-4-methylbenzenesulfonate (51.63g, 0.188mol), reacted at 110 ° C for 36h, after the reaction is completed, it is filtered while hot, the filtrate is collected, and the crude product is obtained by rotary evaporation on a rotary evaporator, then purified by column separation. The selected eluent is dichloromethane. : Acetone (V: V = 15:1), the product was obtained by rotary evaporation to give 16.57 g of pale yellow liquid product, yield 70%.

Reference： [1]Xu, Li; Shao, Lidong; Chen, Lin; Hu, Minqi; Bi, Yunmei [Chemistry Letters, 2010, vol. 39, # 11, p. 1177 - 1179]
[2]Li, Wen; Zhang, Afang; Schlueter, A. Dieter [Chemical Communications, 2008, # 43, p. 5523 - 5525]
[3]Current Patent Assignee: XIANGTAN UNIVERSITY - CN108558701, 2018, A Location in patent: Paragraph 0077; 0078

21
[ 50586-80-6 ]
[ 95-01-2 ]
[ 1172635-12-9 ]

Yield	Reaction Conditions	Operation in experiment
37%	With potassium carbonate In acetonitrile at 60℃; for 48h; regioselective reaction;

Reference： [1]Location in patent: experimental part Gichinga, Moses G.; Striegler, Susanne [Tetrahedron, 2009, vol. 65, # 25, p. 4917 - 4922]

22
[ 50586-80-6 ]
[ 54073-94-8 ]
[ 1186436-44-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With potassium carbonate In N,N-dimethyl-formamide at 60℃; for 3h;

Reference： [1]Shimura, Harutoki; Yoshio, Masafumi; Kato, Takashi [Organic and Biomolecular Chemistry, 2009, vol. 7, # 16, p. 3205 - 3207]

23
[ 50586-80-6 ]
[ 13807-91-5 ]
[ 1194230-68-6 ]

Reference： [1]Chemistry - An Asian Journal,2011,vol. 6,p. 149 - 156
[2]Journal of Organic Chemistry,2009,vol. 74,p. 8154 - 8163

24
[ 50586-80-6 ]
[ 86-74-8 ]
[ 197297-41-9 ]

Yield	Reaction Conditions	Operation in experiment
91%	With sodium hydroxide
91%	With sodium hydride In tetrahydrofuran Reflux;
82%	Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide for 2h; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In N,N-dimethyl-formamide at 20℃; for 24h;	m2 NaH (4.80 g, 200 mmol) with DMF 25 mL were added together into round-bottom flask, then 9H-carbazole (16.70 g,100 mmol) dissolved in DMF was added dropwise using dropping funnel isolating atmosphere. After 2 h m1 (30.10 g, 110 mmol) was added and stirred at 65 oC for 15 h. The mixture was poured into plenty of water and its pH was adjusted to about 6 using diluted hydrochloric acid. Ethyl acetate was used to extract themixture and dried by anhydrous magnesium sulfate. The residue was chromatographed over silica gel. Yellow oily liquid m2 was obtained with yield 82%.

82%	Stage #1: 9H-carbazole With sodium hydride In N,N-dimethyl-formamide at 20℃; for 0.5h; Cooling with ice; Sealed tube; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In N,N-dimethyl-formamide at 65℃; for 15h; Sealed tube;	2 Synthesis of Intermediate 2 The NaH4. 80g (0. 20mol) and DMF 25mL solvent added to the reactor, was added dropwise under ice-bath oils sealing solution of 16. 72g (0. 10 mol) carbazole in DMF was added dropwise to the reaction mixture was stirred at room temperature 30min, then was added 30. 15g (0. llmol) of intermediate 1, the reaction was warmed to 65 ° C 15h, TLC tracking, after completion of the reaction the reaction mixture was poured into ice water, adjusted to pH 5-6 with HCl solution, with ethyl and the combined extracts were dried over anhydrous magnesium sulfate was added, filtered specimens from the filtrate by rotary evaporation to remove the solvent to give a purple liquid column chromatography (eluent by volume ethyl acetate: petroleum ether = 1:10) after to give the intermediate 2-carbazole polyethylene diethylene glycol monomethyl ether 22. lg, as a yellow oil, yield 82%.
80%	Stage #1: 9H-carbazole With sodium hydride at 0℃; for 0.5h; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester at 0 - 20℃;
74%	With sodium hydride In tetrahydrofuran at 20℃; for 5.5h;	2.2.2. Synthesis of 9-(2-(2-methoxyethoxy)ethyl)-9H-carbazole (2) Carbazole (3.34 g, 20 mmol) and sodium hydrogen (0.72 g,30 mmol) were first dissolved in THF (50 mL), then NaH (0.72 g,30 mmol) was added. The solution was stirred for 30 min, compound1 (8.23 g, 30 mmol) was added with constant stirring. The resultingmixture was stirred at room temperature for 5 h. The solution waspoured into icewater, and the productwas extractedwith ethyl acetatethree times. The organic layer was dried over anhydrous magnesiumsulfate filtered and evaporated. The crude product was purified by columnchromatography (ethyl acetate/petroleumether, 1/5, v/v) to affordthe desired compound 2 in 74% yield as yellow oily product. 1H NMR(DMSO d6, 600 MHz) δ (ppm): 8.07 (d, 2H), 7.44 (m, 4H), 7.23 (m,2H), 4.47-4.49 (t, 2H), 3.83-3.85 (t, 2H), 3.49 (m, 2H), 3.40 (m, 2H),3.29 (s, 3H).

Reference： [1]Location in patent: scheme or table Feng, Xin Jiang; Wu, Po Lam; Bolze, Frederic; Leung, Heidi W. C.; Li, King Fai; Mak, Nai Ki; Kwong, Daniel W. J.; Nicoud, Jean-Francois; Cheah, Kok Wai; Wong, Man Shing [Organic Letters, 2010, vol. 12, # 10, p. 2194 - 2197]
[2]Chan; Xu; Guo; Tam; Liu; Chen; Wong; Lo [Organic and Biomolecular Chemistry, 2015, vol. 13, # 26, p. 7307 - 7312]
[3]Kong, Ming; Liu, Yanqiu; Wang, Hui; Luo, Junshan; Li, Dandan; Zhang, Shengyi; Li, Shengli; Wu, Jieying; Tian, Yupeng [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2015, vol. 135, p. 521 - 528]
[4]Current Patent Assignee: ANHUI UNIVERSITY - CN103483389, 2016, B Location in patent: Paragraph 0042; 0043
[5]Niu, Weifen; Jia, Juan; Li, Junkai; Zhang, Chao; Yun, Keming [New Journal of Chemistry, 2019, vol. 43, # 34, p. 13363 - 13370]
[6]Wang, Xiao-dong; Fan, Li; Ge, Jin-yin; Li, Feng; Zhang, Cai-hong; Wang, Juan-juan; Shuang, Shao-min; Dong, Chuan [Spectrochimica Acta Part A: Molecular and Biomolecular Spectroscopy, 2019, vol. 221]

25
[ 40501-41-5 ]
[ 50586-80-6 ]
[ 235110-92-6 ]

Reference： [1]Journal of the American Chemical Society,2008,vol. 130,p. 14840 - 14852

26
[ 3219-63-4 ]
[ 50586-80-6 ]
[ 1254705-77-5 ]

Reference： [1]Journal of Materials Chemistry,2010,vol. 20,p. 8224 - 8226

27
[ 1201-91-8 ]
[ 50586-80-6 ]
[ 1309461-49-1 ]

Yield	Reaction Conditions	Operation in experiment
75%	Stage #1: 4-(N-methyl-N-hydroxyethylamino)benzaldehyde With potassium hydroxide In tetrahydrofuran for 1h; Reflux; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In tetrahydrofuran for 25h; Reflux;

Reference： [1]Location in patent: experimental part Zhao, Yuxia; Wang, Weijia; Wu, Feipeng; Zhou, Yang; Huang, Naiyan; Gu, Ying; Zou, Qianli; Yang, Wei [Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4168 - 4175]

28
[ 50586-80-6 ]
[ 27913-86-6 ]
[ 1257082-58-8 ]

Yield	Reaction Conditions	Operation in experiment
72%	Stage #1: 4-(bis(2-hydroxyethyl)amino)benzaldehyde With potassium hydroxide In tetrahydrofuran for 1h; Reflux; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In tetrahydrofuran for 25h; Reflux;

29
[ 67984-81-0 ]
[ 50586-80-6 ]
[ 1346427-97-1 ]

Yield	Reaction Conditions	Operation in experiment
25%		Step 12-hydroxy-3-(2-(2-methoxyethoxy)ethoxy)benzonitrileTo a solution of <strong>[67984-81-0]2,3-dihydroxybenzonitrile</strong> (13.5 g, 1 eq.) in DMSO (200 mL) was added NaH (60percent, 8 g, 2eq.) and the resulting solution was stirred for 1 h at 60° C. 2-(2-Methoxyethoxy)ethyl 4-methylbenzenesulfonate (20 g, 0.7eq.) in DMSO (100 mL) was added dropwise at 60° C. and stirring was continued for another 1 h.The reaction was quenched by NH4Cl (sat.), the mixture was extracted with EtOAc (300 mL*3) and the combined organic layers were dried over Na2SO4.The solvent was evaporated and the residue was purified by silicon column (EtOAc/PE=1/1) to give the title compound (6 g, 25percent).LC-MS (ES, m/z): 238 [M+H]+

Reference： [1]BioMetals,2011,vol. 24,p. 239 - 258
[2]Patent: US2011/275636,2011,A1 .Location in patent: Page/Page column 30

30
[ 101-98-4 ]
[ 50586-80-6 ]
[ 1351960-19-4 ]

Reference： [1]Organic Letters,2012,vol. 14,p. 330 - 333

31
[ 50586-80-6 ]
[ 51952-13-7 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: sodium hydride / N,N-dimethyl-formamide / 0.5 h / 0 - 20 °C 1.2: 20 °C / Cooling with ice 2.1: palladium 10% on activated carbon; hydrogen / ethyl acetate / 20 h / 20 °C / 11251.1 Torr / Autoclave

Reference： [1]Klein, Jan J.; Hecht, Stefan [Organic Letters, 2012, vol. 14, # 1, p. 330 - 333]

32
[ 67984-81-0 ]
[ 50586-80-6 ]
[ 1204751-09-6 ]

Reference： [1]BioMetals,2011,vol. 24,p. 239 - 258

33
[ 50586-80-6 ]
[ 186663-74-1 ]
[ 126415-03-0 ]

Reference： [1]Polymer,2011,vol. 52,p. 4451 - 4455

34
[ 50586-80-6 ]
[ 186663-74-1 ]
[ 1161412-21-0 ]

Reference： [1]Polymer,2011,vol. 52,p. 4451 - 4455

35
[ 5870-38-2 ]
[ 50586-80-6 ]
[ 116160-23-7 ]

Reference： [1]Bulletin of the Korean Chemical Society,2012,vol. 33,p. 1264 - 1268

36
[ 58749-47-6 ]
[ 50586-80-6 ]
[ 1387641-85-1 ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 3-hydroxy-4-methoxy-6-nitrobenzaldehyde With caesium carbonate In N,N-dimethyl-formamide at 20℃; for 0.5h; Inert atmosphere; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In N,N-dimethyl-formamide at 60℃; for 16h;	70.C 4-Methoxy-5-[2-(2-methoxy-ethoxy)-ethoxy]-2-nitro-benzaldehyde Cesium carbonate (6.90 g, 21.31 mmol) was added to a stirred solution of 5-hydroxy-4-methoxy-2-nitro-benzaldehyde (1.40 g, 7.10 mmol) in DMF (20 mL) at room temperature under nitrogen. After 30 minutes of stirring at the same temperature, toluene-4-sulfonic acid 2-(2-methoxy-ethoxy)-ethyl ester (5.86 g, 21.31 mmol) was added at room temperature and the resulting reaction mixture was stirred at 60° C. for 16 hours (monitored by silica TLC experiment; mobile phase: ethyl acetate-hexanes, 1:4). DMF was distilled off under reduced pressure and the crude material was diluted with ice-water (20 mL) and was extracted with dichloromethane (2*25 mL). Collected organic parts were dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure to give crude 4-methoxy-5-[2-(2-methoxy-ethoxy)-ethoxy]-2-nitro-benzaldehyde as black solid, which was pure enough to proceed for the next step without further purification. (Yield 1.6, 75.3%).

Reference： [1]Current Patent Assignee: ROCHE HOLDING AG - US2012/184548, 2012, A1 Location in patent: Page/Page column 44; 45

37
[ 61160-18-7 ]
[ 50586-80-6 ]
[ 1393456-54-6 ]

Yield	Reaction Conditions	Operation in experiment
68%	With potassium carbonate; In acetonitrile; for 24h;Inert atmosphere; Reflux;	2-Methyl-3-(benzyloxy)-4-(3,6-dioxaheptyloxy)pyridine (19). Flame activated K2CO3 (27.6 g, 0.20 mol) and 16 (27.4 g, 0.10 mol) were added to 18 (21.5 g, 0.10 mol) in dry CH3CN (500 mL). The reaction mixture was heated at reflux for 24 h. After cooling to room temperature, the solvent was evaporated by rotary evaporation. The residue was treated with 10percent NaCl (200 mL) and was extracted with CH2Cl2 (4 × 150 mL). The organic extracts were washed with saturated NaCl (300 mL). After solvent was removed in vacuo, column chromatography using 4:4:2 EtOAc/petroleum ether/acetone furnished 21.5 g of 19 (68percent) as a colorless viscous oil: 1H NMR 2.42 (s, 3 H), 3.34 (s, 3 H), 3.51-3.53 (m, 2 H), 3.69-3.71 (m, 2 H), 3.91 (t, 2 H, J = 4.8), 4.24 (t, 2 H, J = 4.4), 5.02 (s, 2 H), 6.72 (d, 1 H, J = 5.6), 7.31-7.40 (m, 3 H), 7.44-7.49 (m, 2 H), 8.12 (d, 1 H, J = 5.6). 13C NMR 19.34, 59.16, 67.86, 69.45, 70.92, 71.99, 74.57, 106.68, 128.21, 128.45, 128.49, 137.53, 142.32, 145.41, 153.40, 157.64. HRMS m/z calculated for C18H24NO4, 318.1700 (M + H); found: 318.1714. Anal. (C18H23NO4? 0.2 H2O) C, H, N.

Reference： [1]Journal of Medicinal Chemistry,2012,vol. 55,p. 7090 - 7103,14
[2]Patent: WO2015/77655,2015,A1 .Location in patent: Paragraph 00366; 00374

38
[ 3316-09-4 ]
[ 50586-80-6 ]
[ 1203642-89-0 ]

Reference： [1]Organic and Biomolecular Chemistry,2013,vol. 11,p. 5944 - 5953

39
[ 90-01-7 ]
[ 50586-80-6 ]
[ 1342493-70-2 ]

Yield	Reaction Conditions	Operation in experiment
66.2%	With 18-crown-6 ether; potassium carbonate In acetone at 0℃; for 48h; Reflux; Inert atmosphere;	7 2.2.1.1.7 2-{2-(2-Methoxyethoxy)ethoxy}-1-phenylmethynol (6) (Scheme 3) To a mixture of 2-hydroxybenzyl alcohol (5.00 mg, 40.3 mmol), potassium carbonate (11.1 g, 80.6 mmol), and 18-crown-6 (5.35 mg, 20.1 mmol) in dry acetone (200 mL), 5 (12.1 g, 44.3 mmol) dissolved in dry acetone(10 mL) was added dropwise at 0 °C. This solution was refluxed for 48h and allowed to stand for 2 h at 25 °C. After the mixture was filtered, deionized water was added to the resulting solution and the aqueous layer was extracted with CH2Cl2. The combined organic layer was washed with a 2N HCl aq. solution and dried over anhydrous MgSO4 for 1 h. After filtration and concentration, the crude product was purified by silica-gel column chromatography to give 6 as a colorless viscous liquid. Yield: 66.2% (6.00 g). Rf = 0.31 (ethyl acetate/hexane = 1/1 (v/v)). 1H NMR (CDCl3, TMS): δ = 7.35(d, 1H, J = 7.6 Hz, fx2), 7.24(dd, J = 7.6 Hz, J = 8.4 Hz, 1H, fx3), 7.02(dd, 1H, J = 8.4 Hz, J = 8.0 Hz, fx4), 6.90(d, 1H, J = 8.0 Hz, fx5),4.65(d, 2H, J = 5.0 Hz, PhCH2OH), 4.18(t, 2H, J = 4.6 Hz, PhOCH2CH2), 3.83(t, 2H, J = 4.6 Hz, PhOCH2CH2O), 3.67(t, 2H, J = 4.3 Hz, OCH2CH2OCH3), 3.54(t, 2H, J = 4.3 Hz, OCH2CH2OCH3), 3.36(s, 3H, OCH3), 3.33(t, 1H, J = 5.0 Hz, CH2OH).
	With 18-crown-6 ether; potassium carbonate In acetone at 0℃; for 48h; Reflux;	2-[(2-methoxyethoxy)methoxy]benzenemethanol (6) To a mixture of 2-hydroxybenzyl alcohol (5.0 mg, 40.3 mmol), potassium carbonate (11.1 g, 80.6 mmol),and 18-crown-6 (5.35 mg, 20.1 mmol) in dry acetone (200 mL), 2-(2-methoxyethoxy)ethyl4-methylbenzenesulfonate (12.15 g, 44.3 mmol) was added dropwise at 0°C. This solution was refluxed for 48 h and allowed to room tempreture. After the mixture was filtered, it was extracted with CH2Cl2, washed with HCl aq and the organic layer was dried over anhydrous MgSO4. The crude product was purified by silica-gel column chromatography to give 6 as a colorless viscous liquid. Yield: 66.2% (6.0 g).

Reference： [1]Wang, Jianjun; Zang, Yu; Yin, Guanwu; Aoki, Toshiki; Urita, Hiroyuki; Taguwa, Ken; Liu, Lijia; Namikoshi, Takeshi; Teraguchi, Masahiro; Kaneko, Takashi; Ma, Liqun; Jia, Hongge [Polymer, 2014, vol. 55, # 6, p. 1384 - 1396]
[2]Wang, Jianjun; Aoki, Toshiki; Liu, Lijia; Namikoshi, Takeshi; Teraguchi, Masahiro; Kaneko, Takashi [Chemistry Letters, 2013, vol. 42, # 9, p. 1090 - 1092]

40
[ 2432-14-6 ]
[ 50586-80-6 ]
1,3-dibromo-2-[2-(2-methoxyethoxy)ethoxy]-5-methylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
56%	Stage #1: 3,5-dibromo-4-hydroxytoluene With sodium hydride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In tetrahydrofuran at 80℃; Inert atmosphere;

Reference： [1]Cross, Jasmine M.; Fennessy, Rebecca V.; Harding, Lindsay P.; Rice, Craig R.; Hardie, Michaele J.; Slater, Christopher [Chemical Communications, 2013, vol. 49, # 96, p. 11290 - 11292]

41
[ 2563-26-0 ]
[ 50586-80-6 ]
[ 178813-94-0 ]

Yield	Reaction Conditions	Operation in experiment
100%	With potassium carbonate In dimethyl sulfoxide at 80℃;

Reference： [1]Liu, Wei; Liang, Li; Lo, Pik Kwan; Gou, Xiao Jun; Sun, Xiao Hua [Tetrahedron Letters, 2016, vol. 57, # 8, p. 959 - 963]

42
[ 620-18-8 ]
[ 50586-80-6 ]
1-(2-(2-methoxyethoxy)ethoxy)-3-vinylbenzene [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
85%	Stage #1: 3-hydroxystyrene With potassium <i>tert</i>-butylate In acetonitrile for 1h; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In acetonitrile at 70℃; for 10h; Inert atmosphere;	1.2 2) Preparation of 1-(2-(2-methoxyethoxy)ethoxy)-3-vinylbenzene In a 2000 ml round-bottom flask, 55 g of 3-hydroxystyrene was put, 800 ml of acetonitrile was added to dissolve, and 41 g of potassium t-butoxide was added dropwise, followed by reaction for 1 hour. Thereafter, 163 g of 2-(2-methoxyethoxy)ethyl 4-methylbenzenesulfonate was slowly added dropwise, followed by stirring at 70° C. for 10 hours under a nitrogen atmosphere.After the solvent is removed under reduced pressure, it is diluted with normal hexane to crystallize the salt. After filtering the crystallized salt, the organic layer is washed with brine. Then, the solvent was removed under reduced pressure to obtain 86 g (85%) of a brown oil (1-(2-(2-methoxyethoxy)ethoxy)-3-vinylbenzene)

Reference： [1]Current Patent Assignee: LG CHEM CO.,LTD. - KR2021/52965, 2021, A Location in patent: Paragraph 0171; 0176-0180

43
[ 611-99-4 ]
[ 50586-80-6 ]
bis{4-[2-(2-methoxyethoxy)ethoxy]phenyl}ketone [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	Stage #1: 4,4'-Dihydroxybenzophenone With sodium hydride In tetrahydrofuran; N,N-dimethyl-formamide at 0℃; for 1h; Stage #2: toluene-4-sulfonic acid 2-(2-methoxyethoxy)ethyl ester In tetrahydrofuran; N,N-dimethyl-formamide at 60℃; for 72h;	1.1 Step 1: Synthesis of compound C1 At 0°C, into a 100 mL Shrek tube, sodium hydride (0.2 g, 64 mmol) was added, and 30 mL of anhydrous tetrahydrofuran was added. 4,4'-Dihydroxybenzophenone A1 (2.1g, 10mmol)Dissolve in 30ml anhydrous DMF, and slowly add it to the reaction flask with a syringe, stir and react for 1h. B1 (1.5 g, 64 mmol) was added to the reaction system, and the reaction system was heated to 60° C. for 72 hours.Cool to room temperature, add saturated NH4Cl solution to the reaction system,It was extracted three times with ethyl acetate (3×50 ml), the organic phases were combined and washed with brine (50 mL) and water (50 mL) once. Dry with anhydrous sodium sulfate and filter.The solvent was removed by a rotary evaporator to obtain the crude product, which was separated and purified by silica gel column chromatography (eluent: dichloromethane/methanol=40:1) to obtain a yellow oil C1 with a yield of 89%

Reference： [1]Current Patent Assignee: TIANJIN UVOS TECH - CN113603667, 2021, A Location in patent: Paragraph 0061-0066

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[ CAS No. 50586-80-6 ] {[proInfo.proName]}

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[ 50586-80-6 ] Synthesis Path-Upstream 1~4

[ 50586-80-6 ] Synthesis Path-Downstream 1~43

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