Ethylene Glycol → 2-(tert-Butyl(dimethyl)silyl)oxyethanol

Temperature

20 °C

Ethylene glycol (2.00 g) in anhydrous THF (60 ml) under nitrogen was treated portionwise with sodium hydride (60% dispersion in mineral oil, 1.29 g) and the mixture stirred at 20° C. for 45 min. Tert-butyl dimethylsilyl chloride (4.86 g) was added and the mixture stirred at 20° C. for 45 min. Phosphate buffer (60 ml, pH6.5) was added and the mixture stirred for 20 min before extracting with ether (60 ml). The organic layer was then washed with water (60 ml) and brine (60 ml), before drying over Na2SO4, filtering, and removing the solvent in vacuo. This was purified by flash chromatography on silica. Elution with 1:4 EtOAc/cyclohexane followed by solvent evaporation in vacuo gave the title compound (3.82 g). TSP+ve 194 MNH4+.

1. stirringthe mixture stirred at 20° C. for 45 min
2. stirringthe mixture stirred for 20 min
3. extractionbefore extracting with ether (60 ml)
4. washThe organic layer was then washed with water (60 ml) and brine (60 ml)
5. dry with materialbefore drying over Na2SO4
6. filtrationfiltering
7. customremoving the solvent in vacuo
8. customThis was purified by flash chromatography on silica
9. washElution with 1:4 EtOAc/cyclohexane
10. customfollowed by solvent evaporation in vacuo

ORD record

ord-d417a8d2118e492b8cc02a8c0d0abf2d

Source dataset

uspto-grants-2008_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07361787B2