[maverick1996]

Hey guys!!

I am just wondering whether this method would work? And if there is a better way of doing it?

I have attached both the question and my scheme

Thank you

[AWK]

Wrong position of double bond in last two lines.

[maverick1996]

Thank you

[Alwin Kristen]

How would you know that your methyl iodide reacts with lactaldehyde and not with NaOH? Could another base be better? Some big and just strong enought to remove proton from hydroxyl group?

[AWK]

Good remark. Aldehyde also reacts itself in presence of NaOH. Though conditions are theoretically anhydrous. I used CaH₂ or molecular sieves for drying DMSO.

[kriggy]

You could probably get rid of the hydroxy group by use of HI in one step.

Im wondering, if acetone derivative could be used in this, like forming enol-ether and then arylate it with bromobenzene in presence of some metal catalyst

[clarkstill]

Any way you could think of using an epoxide?

[discodermolide]

What about a metal catalysed aryl-vinyl cross coupling?

[maverick1996]

Thank you all for your input, I'm a first year so I'm just going by the reactions that I've already seen but I'll give it a shot with the ways that you have suggested

And about using NaOH - thank you

[subro]

Any way you could think of using an epoxide?

Yeah, I was going to post this.

[phth]

What about a metal catalysed aryl-vinyl cross coupling?

+1 this transformation can be done in 1 step. Ni(II) Hiyama coupling.  Ni is better than Pd.