반응 #912

반응 방정식

HCl

n-butyllithium

N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide

dimethyldisulfide

→

title compound

수율 58.8%

N-(1,1-Dimethylethyl)-1-methyl-2-(methylthio)-1H-pyrrole-3-sulfonamide

수율 58.8%

용매

—

hexanes

THF

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise at such a rate as
2. 2
   기타the temperature below -65° C
3. 3
   기타the resulting reaction mixture
4. 4
   온도to warm to room temperature
5. 5
   workup.STIRRINGstir for ca. 1.5 hours
6. 6
   온도The reaction mixture was cooled to 0° C.
7. 7
   기타The THF phase was separated
8. 8
   세척washed with brine
9. 9
   건조dried (MgSO4)
10. 10
    농축concentrated in vacuo
11. 11
    기타The crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes)

실험 절차

To a solution of 6.48 g (30 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 150 mL THF under nitrogen atmosphere cooled to -78° C. was added dropwise at such a rate as to keep the temperature below -65° C. 25.52 mL (61.5 mmol) 2.41M n-butyllithium in hexanes. The reaction was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added 2.97 mL (33 mmol) of dimethyldisulfide in one portion and the resulting reaction mixture was allowed to warm to room temperature and stir for ca. 1.5 hours. The reaction mixture was cooled to 0° C. and acidified with 1N HCl. The THF phase was separated washed with brine, dried (MgSO4) and concentrated in vacuo. The crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes) affording 4.63 g of the title compound as an off white solid, m.p. 116°-119° C.

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