Reaction mechanism help?

[puppylaugj77]

Hello everyone!

I am trying to write out the mechanism for this reaction. My first step was to deprotonate Carbon 2 to create the double bond between 1 and 2 and remove the oxygen. Is this correct and how do I make the other double bond?

[exchemist]

12 hours ago, puppylaugj77 said:

Hello everyone!

I am trying to write out the mechanism for this reaction. My first step was to deprotonate Carbon 2 to create the double bond between 1 and 2 and remove the oxygen. Is this correct and how do I make the other double bond?

I don't remember much organic synthesis, I'm afraid. I can see how you will get an enol (or enolate, under alkaline conditions) but how do you think the oxygen is removed? 

[puppylaugj77]

On 9/27/2023 at 10:36 AM, exchemist said:

I don't remember much organic synthesis, I'm afraid. I can see how you will get an enol (or enolate, under alkaline conditions) but how do you think the oxygen is removed? 

I realized I’ve made a mistake lol. I don’t know how to remove the oxygen. I’ll try to work on this later. Maybe it has something to do with a Michael addition?

[exchemist]

15 hours ago, puppylaugj77 said:

I realized I’ve made a mistake lol. I don’t know how to remove the oxygen. I’ll try to work on this later. Maybe it has something to do with a Michael addition?

What bothers me is that this looks like a reduction overall, yet I can't see what is being oxidised. Unless it is the methanol.