Triethylamine → (S)-Glycidoxy-t-butyldimethylsilane

To a solution of (R)-glycidol (5 g, 67.5 mmol) in dry dichloromethane containing triethylamine (10.3 ml, 74 mmol) cooled down to 00° 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. temperaturecooled down to 00° C
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-Eintrag

ord-14f7bcec30fc41dba5a0fb741a49016d

Quelldatensatz

uspto-grants-2000_12

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US06160109