반응 #719823

반응 방정식

3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide

(E)-ethyl 3-(4-hydroxyphenyl)-2-methylacrylate

sodium hydride

→

(E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylate

수율 86.0%

용매

DMF

DMF

반응 조건

후처리

1. 1
   온도The reaction was heated to 80° C. for 15 h
2. 2
   온도Upon completion the reaction was cooled to room temperature
3. 3
   기타quenched with water
4. 4
   추출extracted with EtOAc
5. 5
   세척The combined organic layers were then washed with water, sat. aq. NaHCO3, brine
6. 6
   기타collected (phase separator)
7. 7
   농축concentrated in vacuo
8. 8
   기타to afford the crude product
9. 9
   기타The crude material was purified by column chromatography (SiO2, 0-70% EtOAc/Heptane)

실험 절차

To a solution of (E)-ethyl 3-(4-hydroxyphenyl)-2-methylacrylate (92 mg, 0.445 mmol) in DMF (2.0 mL) was added sodium hydride (60% suspension in oil, 17.79 mg, 0.445 mmol), the resulting mixture was allowed to stir for 30 min at room temperature. To the solution was added 3-bromo-6-methoxy-2-(4-methoxyphenyl)benzo[b]thiophene 1-oxide (125 mg, 0.342 mmol) as a suspension in DMF (2.0 mL). The reaction was heated to 80° C. for 15 h. Upon completion the reaction was cooled to room temperature, quenched with water and extracted with EtOAc. The combined organic layers were then washed with water, sat. aq. NaHCO3, brine and then collected (phase separator) and concentrated in vacuo to afford the crude product. The crude material was purified by column chromatography (SiO2, 0-70% EtOAc/Heptane) to afford (E)-ethyl 3-(4-((6-methoxy-2-(4-methoxyphenyl)-1-oxidobenzo[b]thiophen-3-yl)oxy)phenyl)-2-methylacrylate (144 mg, 0.294 mmol, 86% yield). LC/MS (m/z, MH+): 491.3

출처