[MuscarineChloride]

Hello everyone,

I habe been trying to reproduce a reduction reaction of an ethylester (Benzyl-Ethyllactate) to an aldehyde using DiBAL-H in Ethylether at -78 °C in Dry solvents but have been getting basically no product, the solvents an the glasware are dry and the  DiBAL-H is new. Also no alcohol is present...

Any suggestions why my reduction isnt working? The Literature reports up to 80-90 % isolated yield for the same reaction.

[rolnor]

Is diethyl ether the solvent used in the reference?

[MuscarineChloride]

yes diethylether is also the solvent in the refrence

[rolnor]

Do you have NMR of the starting ester?
Do you monitor the reaction in some way, TLC?

[Babcock_Hall]

How dry is your starting material?

[MuscarineChloride]

Yes i have a NMR of the startung ester, it fits the refrence.

I can monitor the reaction by TLC an massspec.

The starting material should be dry, it is dried after the extraction with Na2SO4 and then purifyed on a sillica column, I will dry it a second time and give it an noter try!

[rolnor]

How does it look on MS?

[Babcock_Hall]

There are other more experienced synthetic chemists here than I am.  However, I will share my thoughts.  When I first started to use Dibal-H to attempt the reduction of a Weinreb amide, we obtained poor results.  Much later and with a different batch of Dibal-H, we obtained better yield.  It might or might not have been the Dibal-H itself; it could easily have been other aspects of our technique.

[wildfyr]

Maybe give it a little extra ass kicking by doing at higher temp?