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.
Thursday, July 14, 2011
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.
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.
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