Triethoxychlorosilane → Silane, triethoxyethynyl-

Temperature

23 °C

Chlorotriethoxysilane (2.0 mL, 10 mmol, 1.0 equiv) was added to a stirred solution of 0.5M ethynylmagnesium bromide (20 mL, 10 mmol, 1.0 equiv) in tetrahydrofuran (10 mL) at −78° C. The resulting heterogeneous light brown mixture was immediately warmed to 23° C. and stirred for 1 h. The resulting homogeneous light brown solution was heated to 50° C. and stirred for 4 h. The cooled reaction mixture was concentrated under vacuum. The resulting tan powder was slurried in hexane (50 mL), vacuum filtered, and rinsed with additional hexane (3×25 mL). The filtrates were dried over magnesium sulfate, gravity filtered, and concentrated under vacuum to provide the title compound as a pale yellow oil (1.5 g, 80% yield): IR (thin film) 3252 (w), 2976 (s), 2929 (m), 2913 (w), 2890 (m), 2046 (m) cm−1; 1H NMR (400 MHz, CDCl3) δ 3.90 (q, J=7 Hz, 6H), 2.35 (s, 1H), 1.23 (t, J=7 Hz, 9H).

1. temperatureThe resulting homogeneous light brown solution was heated to 50° C.
2. stirringstirred for 4 h
3. customThe cooled reaction mixture
4. concentrationwas concentrated under vacuum
5. filtrationvacuum filtered
6. washrinsed with additional hexane (3×25 mL)
7. dry with materialThe filtrates were dried over magnesium sulfate, gravity
8. filtrationfiltered
9. concentrationconcentrated under vacuum

ORD record

ord-478d6e4e44144b7fa5cf2ef8b91e555a

Source dataset

uspto-grants-2014_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08658568B2