ChemicalBook CAS DataBase List 1,2-BIS(TOSYLOXY)ETHANE

1,2-BIS(TOSYLOXY)ETHANE synthesis

7synthesis methods

Product Name:1,2-BIS(TOSYLOXY)ETHANE
CAS Number:6315-52-2
Molecular formula:C16H18O6S2
Molecular Weight:370.44

1,2-Bistolyloxyethane can be used as an intermediate in pharmaceutical synthesis. And it can be prepared from p-toluenesulfonyl chloride by reacting with ethylene glycol.

107-21-1 Synthesis

107-21-1
1313 suppliers
$10.00/25g

98-59-9 Synthesis

98-59-9
585 suppliers
$9.00/5g

42772-85-0 Synthesis

42772-85-0
81 suppliers
$58.00/100mg

6315-52-2
185 suppliers
$5.00/1g

Yield:42772-85-0 57% ，6315-52-2 17%

Reaction Conditions:

Stage #1:ethylene glycol with triethylamine in dichloromethane at 0; for 0.333333 h;
Stage #2:p-toluenesulfonyl chloride in dichloromethane at 0 - 20; for 25 h;

Steps:

4.2.1. Ethylene glycol monotosylate and ethylene glycol ditosylate
Ethylene glycol monotosylate and ethylene glycol ditosylatewere prepared using a procedure similar to one described previously[53]. Briefly, ethylene glycol (3.5 mL, 62.9 mmol, 8.0 eq.),triethylamine (3.3 mL, 23.6 mmol, 3.0 eq.), and dicholoromethathane(CH2Cl2, 12 mL) were added to a flask and stirred at0 C for 20 min. A solution of TsCl (1.5 g, 7.9 mmol, 1.0 eq.) in CH2Cl2(13 mL) was added slowly using a syringe over 1 h. The resultingmixturewas warmed to room temperature and stirred for 24 h. TLCindicated complete consumption of TsCl. The reaction mixture waswashed with water (2 10 mL), and the aqueous layer wasextracted with CH2Cl2. Organic layers were combined and evaporated.The products were purified by flash column chromatographyon silica gel using 30% ethyl acetate (EtOAc)/hexanes (Hex) to yieldethylene glycol monotosylate as a colorless oil (970 mg, 57% yield)with >95% purity and ethylene glycol ditosylate as a white crystallinesolid (490 mg, 17% yield) with >96% purity. Ethylene glycolmonotosylate: Rf 0.3 in 30% EtOAc/Hex; 1H NMR (CDCl3,500 MHz) d: 7.81 (d, J 7.1, 2H), 7.36 (d, J 7.1 Hz, 2H), 4.14 (q,J 2.3 Hz, 2H), 3.82 (t, J 1.9 Hz, 2H), 2.45 (s, 3H). Ethylene glycolditosylate: Rf 0.5 in 30% EtOAc/Hex; 1H NMR (CDCl3, 500 MHz) d:7.73 (d, J 8.1 Hz, 2H), 7.34 (d, J 7.7 Hz, 2H), 4.18 (s, 2H), 2.46 (s,3H).

References:

Radaram, Bhasker;Pisaneschi, Federica;Rao, Yi;Yang, Ping;Piwnica-Worms, David;Alauddin, Mian M. [European Journal of Medicinal Chemistry,2019,vol. 182,art. no. 111571]

FullText

107-21-1 Synthesis

107-21-1
1313 suppliers
$10.00/25g

98-59-9 Synthesis

98-59-9
585 suppliers
$9.00/5g

6315-52-2
185 suppliers
$5.00/1g

References

4124-41-8 Synthesis