반응 #362666

반응 방정식

sodium iodide

4-(methylthio)acetophenone

triethylamine

chlorotrimethylsilane

→

1-methylthio-4-[1[(trimethylsilyl)oxy]ethenyl]benzene

수율 101.4%

용매

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   workup.STIRRINGThe reaction was stirred for 3 hours
2. 2
   추출extracted with hexane
3. 3
   건조dried (K2CO3)
4. 4
   농축concentrated in vacuo

실험 절차

Under nitrogen, 11.0 g (66.2 mmol) of 4-(methylthio)acetophenone (prepared in Step 1 of Example 1) and 13.8 mL (99 mmol) of triethylamine in 50 mL of acetonitrile was treated with 12.6 mL (99.3 mmol) of chlorotrimethylsilane at ambient temperature and allowed to stir for 20 minutes prior to the slow addition of a suspension of 14.9 g (99.4 mmol) of sodium iodide in 60 mL of acetonitrile. The reaction was stirred for 3 hours, poured into ice/water, and extracted with hexane. The extracts were combined, dried (K2CO3), and concentrated in vacuo to give 16 g of crude 1-methylthio-4-[1[(trimethylsilyl)oxy]ethenyl]benzene as an oil: NMR (CDCl3) δ 0.26 (s, 9H), 2.48 (s, 3H), 4.39 (d, J=2 Hz, 1H), 4.87 (d, J=2 Hz, 1H), 7.20 (d, J=8 Hz, 2H), 7.50 (d, J=8Hz, 2H).

출처