Re: ORGLIST: Alkylation with Ph-Et-Br

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From: Litviæ Mladen (mladen.litvic$##$belupo.hr)
Date: Thu Nov 23 2006 - 02:32:56 EST

Hi Kamal,

 

Try DBU or even better Hunig base in refluxing acetonitrile (works in alkylation of valine methyl ester) but I think you might have alkylation of carboxylic acid (ester formation) as side reaction. The other side reaction you have is elimination of HBr from phenylethyl bromide and formation of styrene. Therefore you should use an excess of phenylethyl bromide.

 

Mladen

 

________________________________

From: everybody-bounces$##$orglist.net [mailto:everybody-bounces$##$orglist.net] On Behalf Of Kamal Morendha
Sent: Wednesday, November 22, 2006 12:27 PM
To: everybody$##$orglist.net
Subject: ORGLIST: Alkylation with Ph-Et-Br

 

Hi !

 

I'm doing one alkylation reaction involving N-Ethoxycarbonylmethyl-L-Valine & 2-Phenylethyl Bromide as under :

EtOOC-CH2-NHCH-CH(CH3)2-COOH + 2-PhCH2CH2Br -------> EtOOC-CH(CH2CH2Ph)-NHCH-CH(CH3)2-COOH

I tried using K2CO3 in diff. solvents, Na-EtOH, but could not get the conversion at all.

May I get some suggetions for this Alkylation ?

Thanks,
Kamal

 

 

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