Imidazole → Tert-butyl(cyclopent-3-en-1-yloxy)dimethylsilane

Cyclopent-3-en-1-ol (10 g, 118.9 mmol) was dissolved in DMF (100 mL) at 0° C., then 1H-imidazole (17.29 mL, 261.5 mmol) was added, followed by tert-butyl(chloro)-dimethylsilane (21.5 g, 142.7 mmol). The mixture was warmed to room temperature and stirred for 14 h. The mixture was diluted with ethyl acetate (300 mL), washed with 5% aqueous LiCl solution (2×100 mL) and brine (50 mL), then dried over sodium sulfate, filtered, and concentrated. The crude residue was purified by chromatography, eluting with 0-10% EtOAc in hexane, to afford the title compound (17.2 g, 73%) as a colourless clear liquid. δH (250 MHz, CDCl3) 5.66 (s, 2H), 4.53 (tt, J 7.0, 3.6 Hz, 1H), 2.57 (dd, J 15.2, 6.8 Hz, 2H), 2.27 (dd, J 15.3, 3.6 Hz, 2H), 0.89 (s, 9H), 0.06 (s, 6H).

1. washwashed with 5% aqueous LiCl solution (2×100 mL) and brine (50 mL)
2. dry with materialdried over sodium sulfate
3. filtrationfiltered
4. concentrationconcentrated
5. customThe crude residue was purified by chromatography
6. washeluting with 0-10% EtOAc in hexane

ORD record

ord-324455cc6672477e9e2e25b2a1d30bd4

Source dataset

uspto-grants-2016_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09309243B2