반응 #651444

반응 방정식

p-toluenesulfonylchloride

sodium hydride

(E)-3-(1H-pyrrol-3-yl)acrylic acid tert-butyl ester

compound D1

(E)-3-(1H-pyrrol-3-yl)acrylic acid tert-butyl ester

sodium chloride

→

title compound

수율 88.1%

(E)-3-[1-(Toluene-4-sulfonyl)-1H-pyrrol-3yl]-acrylic acid tert-butyl ester

수율 88.1%

용매

tetrahydrofurane

반응 조건

후처리

1. 1
   기타is recooled to −30° C.
2. 2
   workup.STIRRINGstirred for 2.5 hours
3. 3
   온도The suspension is warmed slowly at room temperature
4. 4
   추출The mixture is extracted with ethyl acetate
5. 5
   건조The combined organic phase is dried over sodium sulfate (Na2SO4)
6. 6
   여과Afterwards it is filtered
7. 7
   기타evaporated under vacuo
8. 8
   기타The crude product is purified by silica gel flash chromatography

실험 절차

0.230 g of sodium hydride (60%) is suspended in 6 ml of tetrahydrofurane under nitrogen at −30° C. 1.01 g of (E)-3-(1H-pyrrol-3-yl)acrylic acid tert-butyl ester (compound D1) are added to the suspension and warmed slowly to room temperature and stirred for 30 minutes. Afterwards it is recooled to −30° C. and 1.19 g of p-toluenesulfonylchloride are added and stirred for 2.5 hours. The suspension is warmed slowly at room temperature and 40 ml of saturated aqueous sodium chloride solution are added. The mixture is extracted with ethyl acetate. The combined organic phase is dried over sodium sulfate (Na2SO4). Afterwards it is filtered and evaporated under vacuo. The crude product is purified by silica gel flash chromatography using a gradient of hexane-ethyl acetate from 9:1 to 1:1 to give 1.60 g of the title compound as a pale yellow solid.

출처