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Below is the reaction in question. Will it go like an aldol consensation would, where the base would deprotonate the methyl group of the benzoxazole moiety, the negative charge would be transferred over to the nitrogen and this anion would then bond with the aldehyde? In any way, a drawing of the mechanism would be really helpful. A bonus question: is this a specific type of condensation? (i.e. like aldol)

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Your 2-methyl-1,3-benzoxazole is a masked acetic acid.

Remember that one way to synthesize oxazoles actually starts from aldehydes (and uses TosMIC).

So, yes, the reaction is an aldol condensation where the $\ce{CH}$-active component is carboxylic acid in disguise.

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I think that's correct. You should depronate on the methyl group and perform a normal aldol condensation. Interesting choice of base here. I guess the authors must've tuned this for yield.

The best name here would be aldol, since the nucleophile here is very much like an enolate...

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