Triethylamine → (S)-Glycidoxy-t-butyldimethylsilane

Temperature

0 °C

To a solution of (R)-glycidol (5 g, 67.5 mmol) in dry dichloromethane containing triethylamine (10.3 ml, 74 mmol) cooled down to 0° C., was added a solution of tert-butyldimethylsilyl chloride (11.2 g, 74 mmol) in dry dichloromethane (30 ml). Then DMAP (0.33 g, 2.7 mmol) was added. The mixture was allowed to warm up to room temperature and stirred for 5 hours. The triethylammonium chloride crystals were filtered out and washed with dichloromethane (2×10 ml). The organic solution was washed with brine (2×50 ml) and dried over anhydrous sodium sulfate. The solution was concentrated and passed though a short silica gel column to remove polar impurities, and eluted with hexane/ethyl acetate (3:2). After removing the solvent, a colourless oil was collected and dried in vacuo to provide pure (S)-glycidyl-tert-butyldimethylsilyl ether (10.3 g, 81.2%).

1. temperatureto warm up to room temperature
2. filtrationThe triethylammonium chloride crystals were filtered out
3. washwashed with dichloromethane (2×10 ml)
4. washThe organic solution was washed with brine (2×50 ml)
5. dry with materialdried over anhydrous sodium sulfate
6. concentrationThe solution was concentrated
7. customto remove polar impurities
8. washeluted with hexane/ethyl acetate (3:2)
9. customAfter removing the solvent
10. customa colourless oil was collected
11. customdried in vacuo

ORD record

ord-c9e87557e12f48259a5223b9db8c55ee

Source dataset

uspto-grants-2005_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06861518B2