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[ CAS No. 7460-82-4 ] {[proInfo.proName]}

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Chemical Structure| 7460-82-4
Chemical Structure| 7460-82-4
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Product Details of [ 7460-82-4 ]

CAS No. :7460-82-4 MDL No. :MFCD00026001
Formula : C18H22O7S2 Boiling Point : -
Linear Structure Formula :CH3C6H4SO3CH2CH2OCH2CH2O3SC6H4CH3 InChI Key :VYVPNTJBGPQTFA-UHFFFAOYSA-N
M.W : 414.49 Pubchem ID :316659
Synonyms :
Diethylene glycol di(p-toluenesulfonate);Bis-Tos-PEG2;Oxybis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate);Diethylene glycol ditosylate;7460-82-4
Chemical Name :Oxybis(ethane-2,1-diyl) bis(4-methylbenzenesulfonate)

Safety of [ 7460-82-4 ]

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

Application In Synthesis of [ 7460-82-4 ]

* 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.

  • Downstream synthetic route of [ 7460-82-4 ]

[ 7460-82-4 ] Synthesis Path-Downstream   1~8

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YieldReaction ConditionsOperation in experiment
91% With sodium iodide; In acetone; at 60℃; for 10h; General procedure: NaI (5 g, 33.3mmol) was added to 150 mL of an acetone solution containing tosylate (5 g, 12.1 mmol (12), 10.9 mmol (13) and 9.9 mmol(14)), and the resulting solution was stirred at 60 C for 10 h. After filtering the remaining NaI, the resulting mixture was concentrated in vacuo. The residue was extracted with CH2Cl2. The extract was dried with MgSO4, filtered, and concentrated in vacuo to give 15 (3.6 g, 91%), 16 (3.7 g, 92%), and 17 (3.7 g, 90%).
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  • [ 98-59-9 ]
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YieldReaction ConditionsOperation in experiment
47% Diethyleneglycol (1.25 g, 11.8 mmol) was dissolved in water (3.5 mL) and sodium hydroxide (0.768 g, 19.2 mmol) was added. The mixture was stirred at room temperature until a clear solution was obtained. The mixture was cooled to 0°C and a solution of 4-toluene sulfonylchloride (2.27 g, 1 1.9 mmol) in tetrahydrofuran (30 mL) was dropwise added over a period of 20 minutes. After the addition was completed, the reaction mixture was stirred at 0°C for 1 hour. The reaction mixture was diluted with ethyl acetate (150 mL) and water (40 mL). The organic phase was separated, dried over Na2S04, filtered and the solvents were evaporated under reduced pressure. The residue was purified on HP-Sil SNAP cartridges using a Biotage Isolera One purification system employing an dichloromethane/methanol gradient (100/0 ->100/0) to afford the more polar title compound as a colorless oil (1.47 g, 47 percent). The less polar bis-tosyl derivative was discarded. 1H-NMR (400 MHz, CDCI3) delta = 7.80 (d, 2H), 7.35 (d, 2H), 4.22-4.18 (m, 2H), 3.72-3.66 (m, 4H), 3.55-3.51 (m, 2H), 2.45 (s, 3H)
  • 7
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YieldReaction ConditionsOperation in experiment
78% To a stirred solution of propargyl alcohol (100 mg, 1.8 mmol) in dry DMF (30 mL) was added NaH (60% in oil, 900 mg, 22 mmol) at 0 C under Ar. After stirring for 30 min at room temperature, diethylene glycol bis(p-toluenesulfonate) (2.8 g, 6.7 mmol) was added to the mixture at 0 C. The mixture was stirred for 1 h at room temperature. After quenching with sat. NH4Cl at 0 C, the resulting mixture was extracted with EtOAc (250 mL × 3). The organic layer was washed with brine, dried over Na2SO4, and concentrated in vacuo. The residual oil was purified by silica gel column chromatography with 20% EtOAc in hexane to obtain 1 (410 mg, 78%) as a colorless oil. 1H NMR (270 MHz, CDCl3): δ 2.43 (1H, t, J = 2.6 Hz, H-1), 2.45 (3H, s, CH3 in tosylate), 3.59-3.66 (4H, m, -OCH2CH2O-), 3.70 (2H, m, -OCH2CH2OSO2-), 4.16 (2H, m, HCCCH2O-), 4.17 (2H, m, -OCH2CH2OSO2-), 7.34 and 7.80 (each 2H, m, tosylate); HRMS (ESI-TOF, positive mode): calcd for C14H18O5SNa [M+Na]+ 321.0773, found 321.0771.
60% 250 μL (4.23 mmol) of propargyl alcohol was dissolved in 30 mL of dehydrated dimethylformamide, and 348 mg (8.7 mmol) of 60% sodium hydride was added thereto and stirred at room temperature for 30 minutes. 3.5 g (8.5 mmol) of diethylene glycol bis(p-toluene sulfonate) was added thereto while cooling with ice, thereby starting the reaction. After stirring at room temperature for 1 hour, 15 mL of a saturated aqueous solution of ammonium chloride was added thereto thereby terminating the reaction. 60 mL of water was added thereto, 3 mL of 1M hydrochloric acid was added thereto to adjust pH to be 7, and subsequently the resultant was extracted three times with 100 mL of ethyl acetate. The resultant was washed twice with 3 mL of a saturated aqueous solution of sodium chloride, dried over sodium sulfate and subsequently concentrated under reduced pressure thereby obtaining 3262.5 mg of a mixture of a white solid and a light yellow oily substance. The mixture was subjected to silica gel column chromatography (150 g, 3.0 cm inner diameter×35 cm length) using hexane-ethyl acetate (75:25) as an eluent thereby obtaining 753.0 mg (2.523 mmol; yield 60%) of the titled compound as a colorless clear oily substance.
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