반응 #916

반응 방정식

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

N,N-dimethylformamide

HCl

→

title compound

수율 39.0%

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

수율 39.0%

용매

THF

—

hexanes

반응 조건

후처리

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   온도to warm to room temperature
3. 3
   workup.STIRRINGstir for ca. 2 hours
4. 4
   온도The reaction mixture was cooled to 0° C.
5. 5
   기타The THF phase was separated
6. 6
   세척washed with brine
7. 7
   건조dried (MgSO4)
8. 8
   농축concentrated in vacuo
9. 9
   기타The crude residue was chromatographed on silica (25% ethyl acetate/80% hexanes)

실험 절차

To a solution of 12.96 g (60 mmol) of N-(1,1-dimethylethyl)-1-methyl-1H-pyrrole-3-sulfonamide in 300 mL THF under a nitrogen atmosphere cooled to -78° C. was added dropwise, at such a rate as to keep the temperature below -65° C., 52.35 mL (123 mmol) 2.35M n-butylithium in hexanes. The reaction was stirred at -78° C. for ca. 30 minutes. To the reaction mixture was added 4.64 mL (60 mmol) of N,N-dimethylformamide dropwise. The reaction mixture was allowed to warm to room temperature and stir for ca. 2 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 (25% ethyl acetate/80% hexanes) affording 5.72 g of the title compound as a white solid, m.p. 101.5°-103° C.

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