Hi,
It can be possible as ferrocenyl ethanol is a 2° alcohol, but the problem is with ethylene glycol as it is having two -OH groups. I think, by taking 1:1 ratio of DIAD and PPh3 with 1:1 ratio of the two alcohol may yield the product. Refer: J. Org. Chem., 2003, 68, 8261.
Thank you.
The above cited paper is for phenolic alcohols in sonication, and not aliphatic alcohols. I highly doubt the reaction would yield even a small amount of the coupled ether product since neither alcohol is acidic enough to protonate DEAD/DIAD and drive the reaction forward.
Off of the top of my head, the most direct route would be to add a solution of bromoethanol to the pre-made alkoxide of the ferrocenylethanol (with KOH for example). Beta-elimination may be your most likely by-product, but you should be able to avoid this using a different base or colder temps.
If you don't need an ether link linking as a carbonate should be reasonably straight forward.
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