反应 #944039

反应方程式

3-(3,4-dimethylbenzoyl)-2-methylpropionaldehyde ethylene acetal

4-acetylaminosulfonylaniline

hydrochloric acid

→

title compound

收率 25.3%

1-(4-Acetylaminosulfonylphenyl)-2-(3,4-dimethylphenyl)-4-methylpyrrole

收率 25.3%

溶剂

tetrahydrofuran

反应条件

后处理

1. 1
   workup.WAITAt the end of this time, the mixture was left
2. 2
   温度to cool
3. 3
   萃取The mixture was then extracted three times with ethyl acetate
4. 4
   洗涤washed with a saturated aqueous solution of sodium chloride
5. 5
   干燥The resulting solution was then dried over anhydrous magnesium sulfate
6. 6
   浓缩after which it was concentrated by evaporation under reduced pressure
7. 7
   其他The residue thus obtained
8. 8
   洗涤eluted with a 3:2 by volume mixture of hexane and ethyl acetate
9. 9
   其他crystallised from diisopropyl ether

实验过程

3.26 g (13.1 mmol) of 3-(3,4-dimethylbenzoyl)-2-methylpropionaldehyde ethylene acetal [prepared as described in step (ii) above] and 2.81 g (13.1 mmol) of 4-acetylaminosulfonylaniline were dissolved in a mixture of 52 ml (52 mmol) of 1N aqueous hydrochloric acid and 16 ml of tetrahydrofuran, and the mixture was heated at 70° C. for 1 hour. At the end of this time, the mixture was left to stand to allow it to cool. The mixture was then extracted three times with ethyl acetate. The organic extracts were combined and washed with a saturated aqueous solution of sodium chloride. The resulting solution was then dried over anhydrous magnesium sulfate, after which it was concentrated by evaporation under reduced pressure. The residue thus obtained was applied to a silica gel chromatography column and eluted with a 3:2 by volume mixture of hexane and ethyl acetate and crystallised from diisopropyl ether, to give 1.27 g (yield 25%) of the title compound as a white powder, melting at 192-193° C.

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