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$\begingroup$ Boron trichloride cleaves hindered esters (see pubs.rsc.org/en/content/articlepdf/1971/c2/c29710000667 researchgate.net/publication/… ) so seems a reasonable possibility for this $\endgroup$– WaylanderCommented Jun 15 at 13:04
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$\begingroup$ I think the best approach is to used thionyl chloride, vac down hard and be rigorous in excluding water. $\endgroup$– WaylanderCommented Jun 15 at 18:11
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$\begingroup$ I have the reaction running right now, and it seems there is diester forming (control in MeOH). To the chlorination agent I added quite some pyridine which should work as catalyst as well as an acid scavenger in case any moisture is getting into the flask. Exciting $\endgroup$– raptorlaneCommented Jun 20 at 19:26
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