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CAS No. :77544-68-4 MDL No. :MFCD18433414
Formula : C13H20O6S Boiling Point : -
Linear Structure Formula :- InChI Key :RSUCRUOTLCQWFX-UHFFFAOYSA-N
M.W : 304.36 Pubchem ID :10913735
Synonyms :

Safety of [ 77544-68-4 ]

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
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* 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 [ 77544-68-4 ]

[ 77544-68-4 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 98-59-9 ]
  • [ 112-27-6 ]
  • [ 77544-68-4 ]
  • [ 19249-03-7 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
[2] Journal of Porphyrins and Phthalocyanines, 2013, vol. 17, # 1-2, p. 104 - 117
  • 2
  • [ 77544-68-4 ]
  • [ 6338-55-2 ]
Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
[2] European Journal of Organic Chemistry, 2011, # 9, p. 1641 - 1644
[3] European Journal of Organic Chemistry, 2013, # 35, p. 7952 - 7959
[4] Angewandte Chemie - International Edition, 2015, vol. 54, # 35, p. 10327 - 10330[5] Angew. Chem., 2015, vol. 35, # 37, p. 10467 - 10471,5
[6] Chinese Chemical Letters, 2017, vol. 28, # 4, p. 832 - 838
[7] Bioconjugate Chemistry, 2017, vol. 28, # 9, p. 2284 - 2292
[8] Patent: EP3321279, 2018, A1,
[9] Chinese Chemical Letters, 2018,
  • 3
  • [ 98-59-9 ]
  • [ 112-27-6 ]
  • [ 77544-68-4 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydroxide In tetrahydrofuran; water at 0℃; for 2 h; Triethylene glycol (16.81 g, 112 mmol) was dissolved in 20 mL THF, NaOH solution (6.73 g, 168 mmol in 15 mL H2O). The mixture was cooled down to 0 °C by ice/water bath, then TsCl (25.67 g, 135 mmol) in THF (150) was added dropwise to the mixture and the reaction was started simultaneously. The solution was stirred for another 1 h and the solvent was evaporated. The residue was dissolved in DCM and washed with brine (if there is a lot of salt we can wash first the organic layer with water). After that drying over MgSO4, the crude product was further purified by column chromatography with hexane/ethylacetate (2:1) as eluant, afforded the product as yellow oil; yield: 89percent. 1H NMR (CDCl3): δ = 2.44 (s, 3H, CH3), 3.51-3.70 (m, 12H, 6CH2), 7.34 (d, 2H, Ar-H), 7.80 (d, 2H, Ar-H). MS (MALDI-TOF): m/z calc, 304.1; found, 327.21 [M + Na]+.
88.3% With sodium hydroxide In tetrahydrofuran; water at 20℃; for 6 h; Cooling with ice (3) Take the flask, add 0.532 mοl triethylene glycol, add 50 mL of tetrahydrofuran, then slowly drop the cooled 0.2 moles of aqueous sodium hydroxide solution, stir the mixture for several minutes, Under the addition of 0.134 mol of p-methanesulfonyl chloride solution, one hour after the drop, after the completion of the drop of ice water removed, to room temperature reaction, 5 hours after the reaction to remove the solvent to get white or light yellow liquid, dissolved with ethyl acetate, saturated aqueous sodium chloride solution several times, combined with organic phase anhydrous magnesium sulfate drying. The solvent was removed by filtration to give a colorless or pale yellow oil which yielded 88.3percent yield.
83.94% With triethylamine In dichloromethane 250mL single-neck flask was added triethylene glycol (19.69g, 131.13mmol), solution of p-toluenesulfonyl chloride (5.00g triethylamine (7.96g, 78.68mmol) and dichloromethane (50mL), ice-cooled, 26.23 mmol) was dissolved in dichloromethane (50 mL) of. After completion of the dropwise addition, the reaction system was transferred to room temperature overnight. The solvent was removed by rotary evaporation, the residue was added methylene chloride (a 500 mL) was dissolved, washed with water (a 500 mL) and saturated brine (300mL), dried over anhydrous sodium sulfate. Filtered and the solvent was removed by rotary evaporation to give a colorless oil 6.70g, yield 83.94percent.
79% With N-ethyl-N,N-diisopropylamine In dichloromethane at 5 - 20℃; for 18 h; FIG. 10A shows the synthesis of compound 1. Tosyl chloride (1.00 g, 5.25 mmol) was added at 5° C. to a solution of TEG (triethylene glycol, 1.57 g, 10.5 mmol) in anhydrous methylene chloride (6 mL). This was followed by drop-wise addition of DIPEA (N,N-diisopropylethylamine, 1.0 mL, 5.77 mmol). The water bath was removed and the reaction mixture stirred at room temperature for 18 hours. The resulting mixture was diluted with water (6 mL) and washed with 1 M HCl, brine (2×10 mL), and water (3×10 mL). The solution was dried over sodium sulfate and concentrated under vacuum. The resulting residue was purified by silica gel chromatography (ethyl acetate/hexane 7:3) to obtain the product as yellow oil (1.26 g, 79percent). LEN et al., “Micellar Catalysis Using a Photochromic Surfactant: Application to the Pd-Catalyzed Tsuji-Trost Reaction in Water” J. Org. Chem., 79(2): 493-500 (2014). FIG. 10B shows the 1H NMR 300 of compound 1 CDCl3.
75% With pyridine In dichloromethane at 20℃; for 18 h; Briefly, p-toluenesulfonyl chloride (7.50 g, 40.0 mmol) was added to a solution of triethylene glycol (60.0 g, 40.0 mmol) in pyridine (6.5 mL) and dichloromethane (400 mL) and under nitrogen.
After stirring for 18 hr at room temperature, the solvent was concentrated under reduced pressure.
The residue was dissolved in ethyl acetate (200 mL) and washed with aq. NaCl solution (3*200 mL).
The aq.
extract was back extracted with ethyl acetate (2*100 mL), and the combined ethyl acetate phases were dried over MgSO4.
After filtering and evaporating to dryness the product was purified on a silica column to yield a clear oil (9.30 g, 75percent).
1H NMR (300 MHz, CDCl3, TMS): δ 7.82 (d, 3JHH=8.1 Hz, 2H), 7.36 (d, 3JHH=8.1 Hz, 2H), 7.19 (t, 3JHH=3.6 Hz, 2H), 3.59-3.78 (m, 10H), 2.47 (s, 3H).
13C NMR (75 MHz, CDCl3, TMS): δ 144.86, 132.93, 129.82, 127.96, 72.48, 70.77, 70.34, 69.13, 68.70, 61.74, 21.62. IR (NaCl): v=3421, 2886, 1594, 1358, 1169, 664 cm31 1.
75% With potassium hydroxide In tetrahydrofuran at 20℃; for 5 h; Compound 6-1 (235 g, 1.57 mol) was dissolved in 500 mL of tetrahydrofuran, then potassium hydroxide (41.2 g, 0.57 mmol, 82percent w/w) was added, and then p-toluenesulfonyl chloride 6-2 (100 g, 0.52 mol) was added in batches, and the mixture was stirred at room temperature for 5 hours. The reaction solution was poured into 1200 mL of water, and extracted with ethyl acetate (400 mL*3). The extract liquid was combined and washed with saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure and purified by silica gel column chromatography, with an eluent (petroleum ether:ethyl acetate=1:1), to obtain the target product 6-3 (118 g, 75percent) as a colorless oil. LC-MS: m/z=305[M+H]+.
71% With triethylamine In dichloromethane at 20℃; for 12 h; Inert atmosphere; Cooling with ice The reaction process is as follows: three glycol (262.0mmol), triethylamine (40mmol) and methylene chloride (30 ml) mixed and placed in a 250 ml three flasks; will be to toluene sulfonyl chloride (26mmol) and methylene chloride (35 ml) is placed in the dropping funnel constant and is dropped in the three-mouth flask. The use of balloon under the protection of nitrogen ice salt bath stirring, all melted ice when the temperature of the into stirring at the room temperature, the total reaction time is about 12h. Using thin layer chromatography (TLC) detecting the extent of reaction. When the TLC display in the reactant material point recedes, stopping the reaction. The reaction mixture is cooled to room temperature, water washing three times, the aqueous phase dichloromethane is used for extraction, the combined organic phase with anhydrousMgSO4drying, filtering, then turns on lathe reducing the organic solvent. The final 100 - 200 mesh silica gel column chromatography separation method of purification. The ethyl acetate: dichloromethane=4:1 (V/V) as eluant. At the end of the colorless transparent oily liquid product 5.65g (18.6mmol), yield 71percent.
71.3% With pyridine In dichloromethane at 20℃; for 18 h; Inert atmosphere p-Toiuenesuifonyi chloride (7.50 g, 40.0 mrnoi) was added to a solution oftriethylene glycol (60.0 g, 40.0 mrnoi) in pyridine (6.5 mE) and dichiorornethane (DCM, 400 mL) and under nitrogen. After stirring at room temperature for 18 h, the solvent was removed via rotovap. The residue was dissolved in ethyl acetate (200 rnL) and washed with brine (3x100 mL). The ethyl acetate solution was dried over anhydrous Na2SO4. After filtration, the filtrate was evaporated to dryness to give crude product which was puxfied on a silicacolumn to yield 8-tosyloxy-3,6-dioxooctan-I-ol as a clear oil (868 g, 713percent). Orbitrap ESIMS Caicd. for C13H2O6S 30410 Found 305.11.
60% With triethylamine In tetrahydrofuran at 0 - 25℃; for 18 h; Tnethylene glycol (120 mmol, 3 eq.) was dissolved in anhydrous THF (80 ml) and triethylamine (80 mmol, 2 eq.) was added. At 0 °C p-toluenesulfonyl chloride (40 mmol, 1 eq.) in anhydrous THF (10 ml) wasadded dropwise over 45 mm. The reaction mixture was allowed to warm to room temperature and stirred overnight. The solvent was then removed in vacuo and the crude mixture purified by flash column chromatography using a gradient from 30percent-90 percent Ethyl acetate in heptane.
48% With triethylamine In dichloromethane at 25℃; for 12 h; Triethylene glycol (4.50 g, 30 mmol) and triethylamine (TEA) (8.0 mL) were dissolved in dichloromethane (60 mL). Then, tosylchloride (5.70 g, 30 mmol) was added in one portion. The resulting mixture was stirred for 12 h at 25 oC (Scheme 2). After washing with KHSO4 (1 mol/L, 40 mL) and NaHCO3 (5percent, 40 mL) and drying over anhydrous Na2SO4, the crude product was obtained by evaporation and subsequently purified by column chromatography over silica gel (dichloromethane/MeOH = 100:1, v/v) to obtain the target product 1 as a colorless oil (4.2 g, 14.4 mmol, 48percent).
44.4% With dmap; triethylamine In tetrahydrofuran at 0 - 20℃; for 13 h; To a solution of compound 1 (100 g, 665.90 mmol) in THF (500 ml), was added Et3N (46.15 ml, 332.95 mmol) and DMAP (6.51 g, 53.27 mmol) at r.t. Then PTSC (63.48 g, 332.95 mmol) in THF (200 ml) was dropped to above mixture solution for 1h and stirred at 0 °C. Next the mixture solution was stirred for about 12 h at r.t. The reaction mixture was filtered through a celite pad to remove Et3N.HCl. The solvent was evaporated under vacuum. The crude material was purified by column chromatography (DCM : MeOH = 80:1) to obtain yellow oil (90 g , yield 44.4percent). 1H NMR (400 MHz, CDCl3) δ 7.81 (d, J = 8.3 Hz, 2H), 7.35 (d, J = 8.1 Hz, 2H), 4.22 –4.13 (m, 2H), 3.76 –3.67 (m,4H), 3.62 (s, 4H), 3.60 –3.56 (m, 2H), 2.45 (s, 3H), 2.05 (s, 1H). 13C NMR (100 MHz, CDCl3) δ 144.9, 132.7, 129.8, 127.9, 72.5, 70.6, 70.1, 69.2, 68.5, 61.5, 21.6.
33% With potassium iodide; silver(l) oxide In dichloromethane at 20℃; Into a 250-mL round-bottom flask, was placed a solution of 2-[2-(2-hydroxyethoxy)ethoxy]-ethan-1-ol (1.5 g, 9.99 mmol, 1.00 equiv), Ag2O (3.4 g, 14.98 mmol, 1.50 equiv), KI (0.5 g, 2.99 mmol, 0.30 equiv) in dichloromethane (50 mL) at room temperature. This was followed by the addition of TsCl (2.3 g, 12.06 mmol, 1.20 equiv). The resulting solution was stirred overnight at room temperature. The reaction mixture was then quenched by the addition of water (40 mL). The insoluble solids in the reaction mixture were filtered out and the filtrate was extracted with dichloromethane (40 ml x 3). The organic layers were combined, washed with brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was applied onto a silica gel column during with dichlorome thane/me thanol (1 : 1). This resulted in 1 g (33percent) of 14-[(4-methylbenzenesulfonyl)oxy]-3,6,9,12-tetraoxatetradecan-1-ol as yellow oil.
30%
Stage #1: With sodium hydroxide In tetrahydrofuran at 0℃; for 0.25 h;
Stage #2: at 20℃; for 2 h;
j00524j A solution of triethylene glycol (30 g, 199.7 mmol) in THF (300 mL) wascooled to 0°C and charged with NaOH (11.98 g, 299.7 mmol) and stirred for 15 mm. Thissolution was charged with tosyl chloride (38.07 g, 199.7 mmol) and stirred at room temperature for 2 h. The reaction mixture was concentrated in vacuo and the residue obtained was dilutedwith water (100 mL) and extracted with ethyl acetate (3 X 200 mL). The combined organic layers were dried over anhydrous Na2SO4, filtered and concentrated in vacuo resulting in acrude compound which was purified by chromatography on silica gel, eluting with 2percentmethanol in DCM to give 18.5 g, 30percent yield of the title compound as a colorless oil. ‘H NMR(400 MHz, CDC13): ö = 7.78 (d, J= 8.3 Hz, 2H), 7.33 (d, J= 8.1 Hz, 2H), 4.25 —4.10 (m, 2H),3.75 — 3.60 (m, 6H), 3.63 — 3.52 (m, 4H), 2.43 (s, 3H).
22% With dmap; triethylamine In dichloromethane at 0 - 20℃; for 4 h; Inert atmosphere General procedure: p-TsCI (1.2 eq.) was added dropwise to a mixture of the appropriate di-alcohol, Et3N (1 eq.), and DMAP (cat.) in dry CH2CI2 (0.01 M) under N2 atmosphere with stirring at 0°C. The stirring was continued at room temperature for 4 hours. The reaction was quenched with saturated NH4CI aqueous solution and the whole was extracted with AcOEt. The extract was washed with brine, dried over Na2SO4, and, following solvent evaporation, the crude was purified by flash chromatography. ES154; 2-(2-(2-hydroxyethoxy)ethoxy)ethyl 4-methylbenzenesu Ifonate. It was synthesized from triethylene glycol (1 .000 g, 6.66 mmol). Elution with petroleum etherAcOEt (2:8) afforded ES154 as a waxy solid: 0.450 g (22percent).1H-NMR (CDCI3, 400 MHz)5 2.30 (s, 3H), 2.99 (br s, exchangeable with D20, IH), 3.40-3.63 (m, IOH), 4.02 (t,J=4.8 Hz, 2H), 7.21 (d, J=8.4 Hz, 2H), 7.64 (d, J=8.4 Hz, 2H). 13C-NMR (CDCI3, 100MHz) 521.48, 42.73, 61.39, 68.47, 69.24, 70.06, 70.42, 71.12, 72.46, 127.79, 129.81,132.71, 144.87.
55 g at 0 - 20℃; Inert atmosphere Under the protection of nitrogen, to a 1000ml three-necked flask were added 200 mL pyridine, 120 g BP103a00(1.0eq), stirred and cooled down to 0°C. 151.8g TsCl (1.0eq) was added in batches, stirred for 1h, then slowly warmed up to room temperature, and kept stirring for 3-4h. After the completion of the reaction, the reaction liquid was poured into ice-cold dilute hydrochloric acid solution, extracted with ethyl acetate. The ethyl acetate layer was washed once with dilute hydrochloric acid, washed with saturated sodium bicarbonate, washed with saturated brine, and dried over anhydrous Na2SO4. The solvents were evaporated off at reduced pressure, and chromatographed in a silica gel column to give 55g pure BP103a01.

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  • 4
  • [ 98-59-9 ]
  • [ 112-27-6 ]
  • [ 77544-68-4 ]
  • [ 19249-03-7 ]
Reference: [1] Organic Letters, 2002, vol. 4, # 14, p. 2329 - 2332
[2] Journal of Porphyrins and Phthalocyanines, 2013, vol. 17, # 1-2, p. 104 - 117
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[2] European Journal of Organic Chemistry, 2011, # 9, p. 1641 - 1644
[3] European Journal of Organic Chemistry, 2013, # 35, p. 7952 - 7959
[4] Patent: EP3321279, 2018, A1,
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[2] Patent: EP3321279, 2018, A1,
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Reference: [1] Inorganica Chimica Acta, 2011, vol. 365, # 1, p. 38 - 48
[2] Patent: EP3321279, 2018, A1,
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2-Methoxyethyl 4-methylbenzenesulfonate

Similarity: 0.98

Chemical Structure| 6315-52-2

[ 6315-52-2 ]

Ethane-1,2-diyl bis(4-methylbenzenesulfonate)

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Chemical Structure| 26272-83-3

[ 26272-83-3 ]

Oxetan-3-yl 4-methylbenzenesulfonate

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Chemical Structure| 113826-06-5

[ 113826-06-5 ]

(2R)-(-)-Glycidyl tosylate

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Chemical Structure| 70987-78-9

[ 70987-78-9 ]

(s)-(+)-oxirane-2-methanol p-toluenesulfonate

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