1,2-BIS(TOSYLOXY)ETHANE synthesis
- Product Name:1,2-BIS(TOSYLOXY)ETHANE
- CAS Number:6315-52-2
- Molecular formula:C16H18O6S2
- Molecular Weight:370.44
107-21-1
1375 suppliers
$10.00/25g
98-59-9
625 suppliers
$9.00/5g
42772-85-0
94 suppliers
$58.00/100mg
6315-52-2
214 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]
4124-41-8
303 suppliers
$10.00/5g
107-21-1
1375 suppliers
$10.00/25g
6315-52-2
214 suppliers
$5.00/1g
16836-95-6
148 suppliers
$21.00/1g
106-93-4
404 suppliers
$15.00/5g
6315-52-2
214 suppliers
$5.00/1g
107-21-1
1375 suppliers
$10.00/25g
6315-52-2
214 suppliers
$5.00/1g