반응 #341983

반응 방정식

6-trimethylsilanylethynyl-benzo[1,3]dioxole-5-carbaldehyde

p-aminoacetophenone

cyclopentadiene

→

1-[4-(6-Trimethylsilanylethynyl-benzo[1,3]dioxol-5-yl)-3a,4,5,9b-tetrahydro-3H-cyclopenta[c]quinolin-8-yl]-ethanone

수율 97.0%

용매

acetonitrile

acetonitrile

반응 조건

후처리

1. 1
   기타The reaction mixture was worked up by removal of solvent and other volatiles by evaporation under reduced pressure
2. 2
   기타The crude material was purified by preparative column chromatography
3. 3
   세척eluted with EtOAc/hexane (polar phase composition 8% EtOAc)
4. 4
   workup.ADDITIONThe fractions containing pure product
5. 5
   기타were evaporated in vacuo

실험 절차

A solution of the catalyst Sc(OTf)3 (0.032 g, 0.065 mmol, 10 mol %) in acetonitrile (0.2 mL) was added to the mixture of 6-trimethylsilanylethynyl-benzo[1,3]dioxole-5-carbaldehyde (0.160 g, 0.65 mmol), p-aminoacetophenone (0.0878 g, 0.65 mmol) and cyclopentadiene (0.214 g, 3.25 mmol) in acetonitrile (3 mL). The reaction was stirred at ambient temperature (˜23° C.) and the progress was monitored by thin layer chromatography. The reaction was complete after 2 hr. The reaction mixture was worked up by removal of solvent and other volatiles by evaporation under reduced pressure. The crude material was purified by preparative column chromatography using silica gel (SiO2) eluted with EtOAc/hexane (polar phase composition 8% EtOAc). The fractions containing pure product were evaporated in vacuo. The yield was 97%.

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