Re: ORGLIST: Alkylation with Ph-Et-Br

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From: Sachin Chaphekar (purvi_chaphekar$##$yahoo.com)
Date: Sat Nov 25 2006 - 07:25:10 EST

Dear Kamal, Did you try K2CO3 in acetone and preferably in presence of=
 a PTC? K2CO3 works very well in acetone. You will have to use excess (2-2.=
5 moles) since there is a -COOH gr. as well. Otherwise, try pyridine as an =
HBr scavenger, N,N'-diethylaniline also works equally well. alkoxides are p=
retty strong and you will get messy substances. I don't think its a too dif=
ficult a reaction. In some of cases I have got excellent results simply by =
refluxing the halide and substrate in either dichloromethane or ethyl aceta=
te or even THF. Good luck, Sachin ----- Original Message --=
-- From: Kamal <mailbox$##$invalid> To: everybody$##$orglist=
.net Sent: Wednesday, November 22, 2006 4:57:14 PM Subject: ORGLIST: Al=
kylation 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. solven=
ts, Na-EtOH, but could not get the conversion at all. May I get some=
 suggetions for this Alkylation ? Thanks, Kamal =

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