Triethylene glycol di-p-tosylate → Triethylene Glycol

To a 25 mL schlenk flask with Kontes valve and stirbar under argon 1 (1.67 mmol, 0.423 g) was added and the flask evacuated and backfilled with argon 3×. Anhydrous DMF (12.2 mL) was added via syringe and the solution stirred at rt. Next, anhydrous CsCO3 (3.52 mmol, 1.15 g) was added followed by triethylene glycol ditosylate (0.808 mmol, 0.371 g) and the mixture stirred at rt. The vessel was closed, stirred and heated to 70° C. for ca. 12 h. The reaction was allowed to cool to rt then diluted with ethyl acetate (10 mL), filtered and the solid washed with ethyl acetate (3×100 mL) and filtered. The organic extracts combined and washed with saturated NH4Cl(aq) (25 mL) then washed with brine (3×25 mL) dried over Na2SO4, filtered and the solvent removed by rotovaporation to afford the crude product. Purification by silica plug (ethyl acetate) afforded a white solid (0.464 g; 89% yield). IR (cm−1) 2947, 2884, 1683, 1601, 1476, 1397, 1110; 1H NMR (400 MHz, CDCl3) δ 7.38 (s, 4 H, ArH), 6.13 (s, 4 H, ArCHO2), 4.18 (m, 4 H, ArOCH2—), 4.02 (m, 16 H, OCH2CH2O), 3.84 (m, 4 H, ArOCH2CH2—), 3.78 (s, 4 H, ArOCH2CH2OCH2CH2OCH2CH2OAr), 2.33 (s, 6 H, ArCH3); {1H} 13C NMR (100 MHz, CDCl3) 154.5, 134.2, 130.8, 129.0, 99.1, 76.0, 70.9, 70.5, 65.5, 21.2.

1. additionTo a 25 mL schlenk flask with Kontes valve and stirbar under argon 1 (1.67 mmol, 0.423 g) was added
2. customthe flask evacuated
3. additionAnhydrous DMF (12.2 mL) was added via syringe
4. stirringthe mixture stirred at rt
5. customThe vessel was closed
6. stirringstirred
7. temperatureheated to 70° C. for ca. 12 h
8. temperatureto cool to rt
9. filtrationfiltered
10. washthe solid washed with ethyl acetate (3×100 mL)
11. filtrationfiltered
12. washwashed with saturated NH4Cl(aq) (25 mL)
13. washthen washed with brine (3×25 mL)
14. dry with materialdried over Na2SO4
15. filtrationfiltered
16. customthe solvent removed by rotovaporation

ORD record

ord-bbb303ee795642c3be1f4ccb34539528

Source dataset

uspto-grants-2012_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08182695B2