Trimethylsilylacetylene → HCID 101337817, compound

Temperature

0 °C

In an oven-dried flask, trimethylsilylacetylene (7.02 g, 71.5 mmol) was dissolved in pentane (60 mL), and cooled to 0° C. in an ice bath. n-Butyllithium (26 mL, 2.5 M in hexanes, 65 mmol,) was added dropwise and the temperature was maintained for an hour. Diisopropylchlorosilane (10.0 g, 66.4 mmol) was added slowly, and the suspension was allowed to warm overnight. The reaction was quenched by the addition of water (60 mL) and stirred until all precipitate dissolved. The organic layer was separated, and the aqueous layer was extracted with pentane (40 mL). The organic layers were combined, washed with water (2×20 mL), and dried over magnesium sulfate. The resulting solution was rinsed onto a thin pad of silica and the product was eluted with additional pentane. Solvent was carefully removed from the volatile desired product using a rotary evaporator to yield 14 g (66 mmol, 99%) of a colorless liquid. 1H-NMR (400 MHz, CDCl3) δ=3.6 (s, 1H), 1.0 (m, 14H), 0.1 (s, 9H).

1. temperaturethe temperature was maintained for an hour
2. temperatureto warm overnight
3. customThe reaction was quenched by the addition of water (60 mL)
4. dissolutiondissolved
5. customThe organic layer was separated
6. extractionthe aqueous layer was extracted with pentane (40 mL)
7. washwashed with water (2×20 mL)
8. dry with materialdried over magnesium sulfate
9. washThe resulting solution was rinsed onto a thin pad of silica
10. washthe product was eluted with additional pentane
11. customSolvent was carefully removed from the volatile desired product
12. customa rotary evaporator

ORD record

ord-d3f697554ea94f48a8f212255e178363

Source dataset

uspto-grants-2014_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08809568B2