Chlorotrimethylsilane → Trimethyl((3-methyloxetan-3-yl)ethynyl)silane

Temperature

-78 °C

A 250-mL round-bottom flask was charged with 3-(2,2-dibromovinyl)-3-methyloxetane (2.177 g, 8.51 mmol) in THF (85 mL) to give a clear solution. The flask was cooled in a dry ice/acetone bath for 15 min, then n-butyllithium (7.83 mL, 19.56 mmol) (as a 2.5 M solution in hexane) was added dropwise over five min. After stirring at −78° C. for 45 min, trimethylchlorosilane (3.81 mL, 29.8 mmol) was added over 2 min. The cooling bath was removed after 30 min and the reaction was allowed to warm to RT for 30 min. The mixture was diluted with water (50 mL) and ether (50 mL). The layers were separated, and the aqueous layer was extracted with ether (25 mL). The combined organic extracts were dried over magnesium sulfate, filtered, and evaporated. The residue was dissolved in a small amount of ether and filtered through a small pad of silica gel. The filtrate was evaporated to give trimethyl((3-methyloxetan-3-yl)ethynyl)silane (1.344 g, 7.99 mmol, 94% yield) as a pale-yellow oil.

1. customto give a clear solution
2. temperatureThe flask was cooled in a dry ice/acetone bath for 15 min
3. customThe cooling bath was removed after 30 min
4. temperatureto warm to RT for 30 min
5. additionThe mixture was diluted with water (50 mL) and ether (50 mL)
6. customThe layers were separated
7. extractionthe aqueous layer was extracted with ether (25 mL)
8. dry with materialThe combined organic extracts were dried over magnesium sulfate
9. filtrationfiltered
10. customevaporated
11. dissolutionThe residue was dissolved in a small amount of ether
12. filtrationfiltered through a small pad of silica gel
13. customThe filtrate was evaporated

ORD record

ord-b8067c31888d46a6b92c78b706ef7a43

Source dataset

uspto-grants-2013_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08497265B2