反应详情

To a cold suspension of methyl triphenyl phosphonium iodide (2.88 g, 7.13 mmol) in THF (20 mL) was added KOBt (0.88 g, 7.84 mmol) slowly. The reaction mixture was warmed to RT and stirred for about 1 h. A solution of 4-(2-(tert-butyldimethylsilyloxy)ethoxy)benzaldehyde (1.0 g, 3.56 mmol) in THF (15 mL) was added slowly to the above reaction mixture and stirred for about another 3 h. The reaction was quenched with water and extracted with diethyl ether (3×75 mL). The combined organic extracts were washed with brine (1×75 mL), dried over sodium sulphate and concentrated under reduced pressure. The residue obtained was purified by silica gel chromatography using 10% EtOAc-hexane as the eluent. Relevant fractions containing the target compound were combined and evaporated to dryness under reduced pressure to afford tert-buyldimethyl (2-(4-vinylphenoxy)ethoxy)silane 0.65 g, (65%), 1H NMR (400 MHz, CDCl3): δ 7.350-7.342 (d, J=3.2 Hz, 2H), 6.882-6.875 (d, J=2.8 Hz, 2H), 6.857-6.692 (m, 1H), 5.625-5.581 (d, J=17.6 Hz, 1H), 5.132-5.104 (d, J=11.2 Hz, 1H), 4.052-3.954 (m, 4H), 0.909 (s, 9H), 0.1 (s, 6H), MS m/z: 279.3 (M+H)+.

1. additionwas added KOBt (0.88 g, 7.84 mmol) slowly
2. stirringstirred for about another 3 h
3. customThe reaction was quenched with water
4. extractionextracted with diethyl ether (3×75 mL)
5. washThe combined organic extracts were washed with brine (1×75 mL)
6. dry with materialdried over sodium sulphate
7. concentrationconcentrated under reduced pressure
8. customThe residue obtained
9. customwas purified by silica gel chromatography
10. additionRelevant fractions containing the target compound
11. customevaporated to dryness under reduced pressure