![](/CAS/20180808/GIF/1611489-00-9.gif)
Benzyl-PEG8-THP synthesis
- Product Name:Benzyl-PEG8-THP
- CAS Number:1611489-00-9
- Molecular formula:C28H48O10
- Molecular Weight:544.67
![2-[2-[2-[2-(BENZYLOXY)ETHOXY]ETHOXY]ETHOXY]ETHANOL](/CAS/GIF/86259-87-2.gif)
86259-87-2
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$24.00/1g
![TOS-PEG5-THP](/CAS/20200515/GIF/86259-89-4.gif)
86259-89-4
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$350.00/1g
![Benzyl-PEG8-THP](/CAS/20180808/GIF/1611489-00-9.gif)
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Yield:1611489-00-9 99.3%
Reaction Conditions:
Stage #1: 1-phenyl-2,5,8,11-tetraoxatridecan-13-olwith sodium hydride;sodium iodide in tetrahydrofuran;mineral oil at 0; for 2 h;Inert atmosphere;
Stage #2: 2-(2-(2-(2-((tetrahydro-2H-pyran-2-yl)oxy)ethoxy)ethoxy)ethoxy)ethyl 4-methylbenzenesulfonate in tetrahydrofuran;mineral oil; for 12 h;Reflux;Inert atmosphere;
Steps:
Synthesis of monotetrahydropyran-protectedocta(ethyleneglycol) monobenzyl ether (11)
Pure tetraethylene glycol monobenzyl ether (10b, 71 g, 0.25 mol) in dry THF (200mL) was added to NaH (12.5 g, 60% dispersion in mineral oil, 1.2 equiv.), NaI(2.0 g, 13 mmol) in dry THF (1.3 L) dropwise and stirred for 2 h at 0 oC.A solution of 9a (121.7 g, 0.275 mol,1.1 equiv.) prepared above in THF (300 mL) was added dropwise over 1 h at 0 oCand the resulting reaction mixture was allowed to warm at room temperature andheated slowly to reflux for another 12 h while stirring. After the mixture wasfiltered through Celite 545 to remove the solid, the obtained filtrate was concentratedto remove THF and redissolved in dichloromethane (1 L). After washed withaqueous NaCl/NaOH solution (2 x 300 mL), decolorized by activated charcoal anddried over anhydrous sodium sulfate, the organic layer was concentrated anddried under vacuum to give 11 as areddish viscous liquid (135 g, 99.3%). 1H NMR (500 MHz, CDCl3)δ 7.25-7.37 (m, 5H), 4.64 (t, 1H, J = 5 Hz), 4.58 (s, 2H), 3.83-3.92 (m,2H), 3.59-3.72 (m, 33H), 3.51 (m, 1H), 1.79-1.89 (m, 1H), 1.68-1.77 (m, 1H),1.47-1.66 (m, 4H); 13C NMR (125 MHz, CDCl3) δ 138.26,128.28, 127.66, 127.50, 98.88, 73.18, 70.50-70.61 (br.), 69.41, 66.60, 62.14,30.53, 25.40, 19.43. HRMS(m/z) calcd for C28H48NaO10+,567.3150 [M+Na]+, found 567.3170.
References:
Zhang, Quanxuan;Ren, Hong;Baker, Gregory L. [Tetrahedron Letters,2014,vol. 55,# 22,p. 3384 - 3386] Location in patent:supporting information
![Bis[2-(2-hydroxyethoxy)ethyl] ether](/CAS/GIF/112-60-7.gif)
112-60-7
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![Benzyl-PEG8-THP](/CAS/20180808/GIF/1611489-00-9.gif)
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![3,4-Dihydro-2H-pyran](/CAS/GIF/110-87-2.gif)
110-87-2
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$10.00/1g
![Benzyl-PEG8-THP](/CAS/20180808/GIF/1611489-00-9.gif)
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![THP-PEG5](/CAS/20200515/GIF/128660-97-9.gif)
128660-97-9
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$45.00/10mg
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![Benzyl bromide](/CAS/GIF/100-39-0.gif)
100-39-0
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