Imidazole → tert-Butyl(dimethyl)[(prop-2-yn-1-yl)oxy]silane

Temperature

0 °C

To a solution of propargyl alcohol (15 g, 267 mmol) in DMF (60 mL), imidazole (21.85 g, 321 mmol) was added at 0° C. followed by the slow addition of a solution of TBDMS-Cl (47.2 mL, 272 mmol) in DMF (70 mL). Resulting reaction mixture was stirred at 0° C. for 30 min and then at room temperature for overnight. On completion, water was added to the reaction mixture and the aqueous layer extracted with 20% ethyl acetate/hexane. The combined organic layers were dried over sodium sulfate and concentrated to obtain crude material which was purified by column chromatography over silica gel affording tert-butyldimethyl(prop-2-yn-1-yloxy)silane (45.5 g, 32.9%).

1. customResulting
2. customreaction mixture
3. waitat room temperature for overnight
4. extractionthe aqueous layer extracted with 20% ethyl acetate/hexane
5. dry with materialThe combined organic layers were dried over sodium sulfate
6. concentrationconcentrated
7. customto obtain crude material which
8. customwas purified by column chromatography over silica gel

ORD record

ord-e91a91c3ef614492ac41ad2f0f1eb49e

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598167B1