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Topic: Diethyl Malonate --> Methylbutanal  (Read 3976 times)

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red rover189

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Diethyl Malonate --> Methylbutanal
« on: March 23, 2006, 04:03:03 PM »
I've been trying for quite some time to do this problem. We need to find the reagent or reagents that would facilitate the following reaction.

How would one go about converting diethyl malonate (C7H12O4) into 2-methylbutanal (C5H9O)? I believe one would use NaOEt in order to remove a H, create a ring (which would lead to some rearrangement insothat there would be a butyl doublebonded to an O) but I don't know how to "pull off" a methylbutanal.

Any suggestions?

 ???kate
« Last Edit: March 23, 2006, 04:09:54 PM by red rover189 »
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Offline cofi

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Re:Diethyl Malonate --> Methylbutanal
« Reply #1 on: March 23, 2006, 04:37:53 PM »
first NaOEt to remove the hydrogen, then 1m CH3I, then 1m CH3CH2Br, then decarboxylation and finally reduce the -COOH to -CHO :)
« Last Edit: March 23, 2006, 04:38:29 PM by cofi »
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Offline Albert

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Re:Diethyl Malonate --> Methylbutanal
« Reply #2 on: March 23, 2006, 04:39:13 PM »
Hi Kate, Take a look at what I consider a predictable pathway.
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o alquimista

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Re:Diethyl Malonate --> Methylbutanal
« Reply #3 on: March 26, 2006, 09:28:11 AM »
Shouldn't the ethene CH2=CH2 be iodoethane CH3CH2I?
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