Chlorotrimethylsilane → (6-Chlorohex-1-yn-1-yl)trimethylsilane

Temperature

-78 °C

To a solution of 6-chlorohex-1-yne (100 mL, 94.6 g, 0.82 mol) in anhydrous Et2O (500 mL) at −78° C., n-butyllithium (2.5 M in hexane, 360 mL, 0.90 mol) was added over 40 minutes. The resulting mixture was stirred for 30 minutes at −78° C. Chlorotrimethylsilane (125 mL, 1.0 mol) was then added. The mixture was allowed to warm to room temperature and stirred for 16 h. The reaction mixture was carefully quenched with saturated aqueous NH4Cl (300 mL) at room temperature and extracted with Et2O (2×200 mL). The combined organic layers were washed with brine (200 mL), dried over anhydrous Na2SO4, and concentrated in vacuo to afford the title compound (144 g, yield 93%). 1H NMR (DMSO-d6, 400 MHz): δ 3.65 (t, 2H), 2.25 (t, 2H), 1.82-1.75 (m, 2H), 1.58-1.51 (m, 2H), 0.12 (s, 9H).

1. temperatureto warm to room temperature
2. stirringstirred for 16 h
3. customThe reaction mixture was carefully quenched with saturated aqueous NH4Cl (300 mL) at room temperature
4. extractionextracted with Et2O (2×200 mL)
5. washThe combined organic layers were washed with brine (200 mL)
6. dry with materialdried over anhydrous Na2SO4
7. concentrationconcentrated in vacuo

ORD record

ord-191fdb3695bf4929a048d89911423769

Source dataset

uspto-grants-2012_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08299112B2