You might want a second opinion on the ring grignardnecessity, as it is just my personal theory.
BTDT, grignard is very difficult to start. BuLi/MeI works better.
BTDT, grignard is very difficult to start. BuLi/MeI works better.
Dearest hest: What does BTDT mean? And I am unaware of how MeI would produce DOM. Could you tell me, please. :)
I just had an idea:
Could one react acetone enolate with the bromine to get the phenylacetone derivative, then reduce the carbonyl with LAH to get DOPr?
PrimoPyro
Correction: Yellium, how does Bu/Li couple MeI with DOB?
It doesn't. You can't prepare a Lithium/Gringnard reagent in the presence of an amine. But, here's the route I would take:
2,5-Dimethoxybenzaldehyde -> 2-(2,5-dimethoxyphenyl)-[1,3]dioxolane -> 2-(4-Bromo-2,5-dimethoxyphenyl)-[1,3]dioxolane -> 2-(2,5-Dimethoxy-4-Phenyllithium)-[1,3]dioxolane -> -> 4-Methyl-2,5-Dimethoxybenzaldehyde -> -> DOM
Start with 2,5-Dimethoxybenzaldehyde, react that with Ethylene Glycol and catalytic p-Toluenesulfonic Acid to get your dioxolane acetal. Then run that with N-Bromosuccinimde in Acetonitrile for 4 hours at 20°C to get 2-(4-Bromo-2,5-Dimethoxyphenyl)-[1,3]dioxolane. Lithiate that in THF with n-Butyllithium, then add MeI or PrI dropwise to the solution. Then you can get your aldehyde back by treating it with 5%HCl in THF. Whalah!