반응 #58827

반응 방정식

ethynyl(trimethyl)silane

2-(3-bromophenyl)-1,3-dioxolane

N,N-dimethylformamide

triethylamine

→

{[3-(1,3-dioxolan-2-yl)phenyl]ethynyl}-(trimethyl)silane

수율 74.9%

용매

water

반응 조건

후처리

1. 1
   기타was bubbled with anhydrous argon for 5 minutes
2. 2
   온도cooled to room temperature
3. 3
   추출extracted with ethyl ether
4. 4
   건조dried over MgSO4
5. 5
   농축concentrated in vacuo

실험 절차

A mixture of ethynyl(trimethyl)silane (36 g, 367 mmol), 2-(3-bromophenyl)-1,3-dioxolane (78 g, 342 mmol), N,N-dimethylformamide (400 mL), and triethylamine (1.1 81 mL, mmol) was bubbled with anhydrous argon for 5 minutes, treated with copper iodide (0.94 g, 4.96 mmol) and dichlorobis(triphenylphosphine) palladium(II) (7.7 g, 11.01 mmol), stirred at 60° C. for 3 hours, cooled to room temperature, poured into water and extracted with ethyl ether. The organic extracts were combined, dried over MgSO4 and concentrated in vacuo to give {[3-(1,3-dioxolan-2-yl)phenyl]ethynyl}-(trimethyl)silane as a yellow oil (63 g, 256 mmol). The yellow oil was dissolved in MeOH (600 mL) and CH2Cl2 (600 mL), treated with cesium carbonate (91.8 g, 281.6 mmol), stirred at room temperature for 10 h, poured into water and extracted with ethyl ether. The ether extracts were combined, dried over MgSO4, concentrated in vacuo and distilled to give 2-(3-ethynylphenyl)-1,3-dioxolane as a yellow oil (42 g, 71% yield), MS m/e M+ 174; 1H NMR (400 MHz, DMSO-d6) 3.9-4.05 (m, 4H), 4.15 (s, 1H), 5.7 (s, 1H), 7.35-7.45 (m, 4H).

출처