This is what we have seen earlier with silyl ethers which are used as protecting groups for alcohols when strong a base is present in the reaction mixture. Once the acid group is esterified, such selectivity towards this reagent is lost. A protective group (also referred to as "protecting group") is a reversably formed derivative of an existing functional group in a molecule. Protecting Groups: A Necessary Evil 3 Note, however, that each protecting group incorporated in a multi-step synthesis increases the synthesis by two non-productive steps reducing the overall yield and efficiency of the synthesis. If reaction is desired only at the ester site, the keto- group should be selectively protected as an acetal. Acetals and ketals are readily deprotected under neutral conditions in the presence of acetone and indium(III) trifluoromethanesulfonate as catalyst at room temperature or mild microwave heating conditions to give the corresponding aldehydes and ketones in good to excellent yields.

… So, what we do is first react the molecule with a diol forming a cyclic acetal, then reduce the ester with LiAlH 4 to an alcohol, and lastly, remove the protecting acetal by acid catalysis: In the next step, the grignard reaction is carried out. Deprotection. Benzylidene acetal >> Stability: What are protective groups? The reagent attacks at both sites.


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