Thursday, July 14, 2011

A failed reduction by LAH

The reduction by LAH on the following compound failed to give the desired product.
Instead, the allyl alcohol isolated.
So mechanismly, the hydride added to the double bond and the so-formed carbon anion caused the nitrile on the alpha position to eliminate.
But whether the ester is reduced before it or after is not clear now.

Preparation of 1,2-diMagnesiummethylbenzene

The  1,2-dimagnesiummethylbenzene showing below is a useful reagent for metal ligand preparation.
This di-grignard reagent  can be made in high yield from corresponding dichloride compound.

1,2-Dibromomethylbenzene can't be used because it can cause problem.

steps:
1. activate Mg using 1,2-dibromoethane.
2. in diluted solution, slowly add dichloride into Mg in THF. control temperature at rt.
3. allow 8 hr stirring at rt.

yield is over 95% in reports.