Malonic acid + pyridine : Verley-Doebner synthesis

Brett Evill Follow

Thankss!!

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Andrew Goh Follow

As seen in the link I posted before.

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Andy C Follow

Quote from:

I think the last eliminationstep is catalyzed by acid and therefore the weak pyridine as base and the malonic acid rather than malonic ester is used. Even if pyridine is a weak base there will be some of the malonic CH2-groups deprotonated, its a equilibrium.

The small amount of malonic molecules with the CH2- group deprotonated also has the COOH group deprotonated?

Or it can be some molecule with the -COOH not deprotonated but CH2 deprootnated?

Thanks

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Alex Follow

I think the last eliminationstep is catalyzed by acid and therefore the weak pyridine as base and the malonic acid rather than malonic ester is used. Even if pyridine is a weak base there will be some of the malonic CH2-groups deprotonated, its a equilibrium.

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Bernd Leps Follow

Yes, the COOH will also be deprotonated.

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Angel Wallace Follow

I am also wondering, normally Malonicesters are used. But its a modification of Knoevenagel reaction. All acidic H+ will be removed by pyridin, see link.

https://illumina-chemie.de/viewtopic.php?t=4791

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