I am very confused, I think using reduction would be a good start, but LiAl would go straight to an OH. enter image description here


1) As you say*, the ketone must be protected. Protect it. Any propagating naughtiness is irrelevant to the next step.
2) Reduce the ester. Beat on it.
3) Deprotect the ketone.

*Note that you begin with an alpha-ketoester. In the old Morrison and Boyd that was a French joke. LAH would have the same problem. How the mighty have fallen.


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