ORGLIST:puzzle

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From: feng_gu$##$cabot-corp.com
Date: Wed May 21 2003 - 17:15:55 EDT


I was trying to alkylate ethyl 2-methylacetoacetate (90% pure, Aldrich).
When I put the reagent into EtONa/EtOH solution, before I put alkyl halide
into the mixture, it eventually formed a gel ! I try another solvent
system, NaH/THF, and the same thing happened. Anybody can give me an
explanation ? I have never seen this with two step's alkylation of diethyl
malonate. The gel can be redissolved in dil HCl. The amount of reagent I
used was 100 mmol of acetoacetate in roughly 200 ml of solvent. Aldirch's
reagent seems to be the right one with NMR.

Thanks.

FG

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