Topic: Adding an ether group to a silyl enol ether (Read 2535 times)

lrw281 · « **on:** November 18, 2014, 12:05:31 PM »

Could anyone suggest reagents and conditions for this reaction please? I've never seen this before, but I was thinking it would be like adding an alkyl group and a bromine or chlorine would be attached to the group and the double bond would attack the carbon it's attached to and it would leave?
Many thanks in advance

discodermolide · « **Reply #1 on:** November 18, 2014, 12:57:51 PM »

The silyl enol ether is a masked nucleophile at the beta carbon of the double bond, this you know. So how do generate this nucleophile?
Hint, think about things that will attack at silicon then push electrons.

lrw281 · « **Reply #2 on:** November 18, 2014, 01:21:33 PM »

Would reacting it with something like MeLi or BuLi, getting rid of the TMS work?

discodermolide · « **Reply #3 on:** November 18, 2014, 01:37:23 PM »

Not really, it has to be a silylophile. Try looking up deprotection of silyl ethers.

lrw281 · « **Reply #4 on:** November 18, 2014, 05:47:40 PM »

ZnBr₂ and H₂O in CH₂Cl₂? Then what would it react with?

discodermolide · « **Reply #5 on:** November 18, 2014, 05:58:11 PM »

What about a source of fluoride? n-Bu₄N⁺F^- for example. The Si-F bond is very strong so you have thermodynamics working for you.

Topic: Adding an ether group to a silyl enol ether (Read 2535 times)

lrw281

Adding an ether group to a silyl enol ether

discodermolide

Re: Adding an ether group to a silyl enol ether

lrw281

Re: Adding an ether group to a silyl enol ether

discodermolide

Re: Adding an ether group to a silyl enol ether

lrw281

Re: Adding an ether group to a silyl enol ether

discodermolide

Re: Adding an ether group to a silyl enol ether

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