I'm not so sure how this mechanism is supposed to go. Could anyone provide some pointers?

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The answer is supposed to be:

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In particular, I'm confused about how to break up the two esters.

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    $\begingroup$ Google “malonic ester synthesis”, there might be a few helpful pages. $\endgroup$ – orthocresol Apr 24 '18 at 14:32
  • $\begingroup$ What do you know about the stability of 1,3-dicarboxylic acids? $\endgroup$ – Waylander Apr 24 '18 at 14:46
  • $\begingroup$ Possible duplicate of chemistry.stackexchange.com/questions/19410/… $\endgroup$ – Mithoron Apr 24 '18 at 15:45