反应详情

1-(4-octylphenyl)but-3-en-1-ol (11.5 g, 44.2 mmol) and imidazole (3.16 g, 46.4 mmol) were combined in DMF (221 ml). Tert-butyldimethylchlorosilane (6.66 g, 44.2 mmol) was added and the reaction stirred for about 72 h. The reaction was quenched by addition of water and ethyl acetate (500 mL). The layers were separated. The aqueous layer was extracted with ethyl acetate (2×100 mL). The combined ethyl acetate extracts were washed with 5% LiCl solution (3×). The combined extracts were washed with brine, dried over sodium sulfate, filtered, and evaporated to provide tert-butyldimethyl(1-(4-octylphenyl)but-3-enyloxy)silane (19.108 g, 51.0 mmol, 115% yield) as a colorless oil. LC/MS (method f) Rt=5.32, 3.89 min.; MS m/z: 243.21 (M-OTBDMS)+.

1. customThe reaction was quenched by addition of water and ethyl acetate (500 mL)
2. customThe layers were separated
3. extractionThe aqueous layer was extracted with ethyl acetate (2×100 mL)
4. washThe combined ethyl acetate extracts were washed with 5% LiCl solution (3×)
5. washThe combined extracts were washed with brine
6. dry with materialdried over sodium sulfate
7. filtrationfiltered
8. customevaporated