[emyonee]

Hello All,

Please can anyone suggest how I can achieve synthesis in the picture below? I know reduction of the ketone followed by dehydration may work but I'm afraid the ester on the para position may become hydrolyzed during the work up of the reduction. Thanks. 

[AWK]

There are many methods of dehydration.

[rolnor]

You could use DIBAL for the reduction, I think it would be selective at low temperature and not basic in the workup.

[emyonee]

Thanks for your reply
Yes there a different methods for dehydration. However, the work up for the reduction of the ketone will also hydrolyze the ester on the para position

There are many methods of dehydration.

[emyonee]

Thanks for your reply.
It seem DIBAL will also reduce the ester to some extent.

You could use DIBAL for the reduction, I think it would be selective at low temperature and not basic in the workup.

[critzz]

https://en.wikipedia.org/wiki/Carbonyl_reduction#/media/File:Hydride_reduction_table.png

[Vidya]

I think it is better to take care of everything ...
If you think that ester is hydrolyzed  ...then regenerate it after going upto alkene.