反应 #912

反应方程式

HCl

n-butyllithium

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

dimethyldisulfide

→

title compound

收率 58.8%

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

收率 58.8%

溶剂

—

hexanes

THF

反应条件

后处理

1. 1
   workup.ADDITIONwas added dropwise at such a rate as
2. 2
   其他the temperature below -65° C
3. 3
   其他the resulting reaction mixture
4. 4
   温度to warm to room temperature
5. 5
   workup.STIRRINGstir for ca. 1.5 hours
6. 6
   温度The reaction mixture was cooled to 0° C.
7. 7
   其他The THF phase was separated
8. 8
   洗涤washed with brine
9. 9
   干燥dried (MgSO4)
10. 10
    浓缩concentrated in vacuo
11. 11
    其他The crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes)

实验过程

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.

来源