반응 #1884944

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N-(2-Allylsulfanyl-ethyl)-3-pyrrol-1-yl-propionamide

Meta-chloroperoxybenzoic acid

→

meta-chlorobenzoic acid

수율 60.0%

용매

dichloromethane

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후처리

1. 1
   온도The reaction mixture was cooled to between 0-4 C
2. 2
   workup.STIRRINGthe reaction stirred at 0-4 C for 16 hours
3. 3
   기타The solvent was removed in vacuo and purification by flash chromatography on silica
4. 4
   세척eluting with ethyl acetate

실험 절차

N-(2-Allylsulfanyl-ethyl)-3-pyrrol-1-yl-propionamide (0.3704 g, 1.554 mmol, 1 equiv) was taken up in 100 ml of dichloromethane with stirring under nitrogen. The reaction mixture was cooled to between 0-4 C. Meta-chloroperoxybenzoic acid (0.4815 g, 2.790 mmol, 1.8 equiv) was added to the mixture and the reaction stirred at 0-4 C for 16 hours. The solvent was removed in vacuo and purification by flash chromatography on silica: eluting with ethyl acetate gave the by-product meta-chlorobenzoic acid. Further elution with the solvent mixture was gradually changed to a 1:1 ethyl acetate/ethanol gave the product which was isolated by removal of the solvent in vacuo as off-white crystals in 60% yield.

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