反応 #912

反応方程式

HCl

n-butyllithium

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

dimethyldisulfide

→

title compound

収率 58.8%

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

収率 58.8%

溶媒

—

hexanes

THF

反応条件

後処理

1. 1
   workup.ADDITIONwas added dropwise at such a rate as
2. 2
   その他the temperature below -65° C
3. 3
   その他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
   その他The THF phase was separated
8. 8
   洗浄washed with brine
9. 9
   乾燥dried (MgSO4)
10. 10
    濃縮concentrated in vacuo
11. 11
    その他The crude residue was chromatographed on silica (20% ethyl acetate/80% hexanes)

実験手順

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.

出典