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Topic: Synthesizing 1 p toluenesulfonylpyrrole  (Read 4704 times)

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Offline surayutaka

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Synthesizing 1 p toluenesulfonylpyrrole
« on: August 20, 2012, 02:32:10 AM »
Measure 2,5-dimethoxytetrahydrofuran into a flask. Add p-toluenesulfonamide and acetic acid. Heat at reflux for two hours.

Q: What is the function of acetic acid in this synthesis?

I guess its a solvent and acid catalyst? Any take?


Offline discodermolide

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Re: Synthesizing 1 p toluenesulfonylpyrrole
« Reply #1 on: August 20, 2012, 02:36:23 AM »
Measure 2,5-dimethoxytetrahydrofuran into a flask. Add p-toluenesulfonamide and acetic acid. Heat at reflux for two hours.

Q: What is the function of acetic acid in this synthesis?

I guess its a solvent and acid catalyst? Any take?



2,5-dimethoxytetrahydrofuran is effectively an acetal, the acetic acid will cause ring opening allowing the toluenesulfonamide to attack with following ring closure.

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Offline surayutaka

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Re: Synthesizing 1 p toluenesulfonylpyrrole
« Reply #2 on: August 20, 2012, 06:04:23 AM »
Thanks. Will the acid be reformed after the reaction in this case?

Offline surayutaka

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Re: Synthesizing 1 p toluenesulfonylpyrrole
« Reply #3 on: August 20, 2012, 06:28:07 AM »
its fine! i got it! :) its just a standard pyrrole synthesis  ;D

Offline discodermolide

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Re: Synthesizing 1 p toluenesulfonylpyrrole
« Reply #4 on: August 20, 2012, 06:32:12 AM »
its fine! i got it! :)

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