Hexane → (3-Cyclopropylprop-1-yn-1-yl)trimethylsilane

Temperature

-78 °C

A 500 mL three-necked round bottom flask was charged with (trimethylsilyl)acetylene (15 g, 153 mmol) and dry THF (75 mL). The solution was cooled to −78° C., and a solution of n-butyllithium in hexane (2.5 M, 75 mL, 188 mmol) was added dropwise over 30 minutes. The resulting mixture was stirred at 0° C. for 10 minutes and then re-cooled to −78° C. HMPA (40 g, 223 mmol) was added, and the mixture was stirred at −78° C. for 30 minutes. (Bromomethyl)cyclopropane (20.6 g, 153 mmol) was then added. The reaction mixture was allowed to warm to room temperature and stirred overnight. Upon completion, the reaction mixture was washed with water (4×100 mL) and brine (2×100 mL) sequentially. The organic layer was dried over anhydrous sodium sulfate. Hexane and THF was distilled off at 75˜110° C. then distillation at 138˜142° C. afforded the title compound (12 g). 1H NMR (400 MHz, DMSO-d6): δ 2.27 (d, 2H), 0.91-0.84 (m, 1H), 0.43-0.34 (m, 2H), 0.19-0.14 (m, 2H), 0.11 (s, 9H).

1. temperaturere-cooled to −78° C
2. stirringthe mixture was stirred at −78° C. for 30 minutes
3. temperatureto warm to room temperature
4. stirringstirred overnight
5. washUpon completion, the reaction mixture was washed with water (4×100 mL) and brine (2×100 mL) sequentially
6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
7. distillationHexane and THF was distilled off at 75˜110° C.
8. distillationdistillation at 138˜142° C.

ORD record

ord-4f9c73e9d413475c970459befce3e475

Source dataset

uspto-grants-2016_07

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09399646B2