[Nikola95]

One more question: Dont you need to protect the other carbon in acetylene when doing the coupling reaction? So you dont get acetylene substitued on both carbons.

No, you don`t have to. As I have written, by using one equivalent of a base, acetylene can be gradually alkylated in the great yields. Look at my method.

[TheQuestion90]

Thank you all for your assistance I very much appreciate it!!!

[zsinger]

Giggity…..Suzuki Coupling…….Giggity…...  That is a reaction that should be mandatory in all organic classes, as it could have turned this problem into fewer steps!
            -Zack

[zsinger]

I am somewhat sure that this is not the 100% correct answer……while you are correct that stoichiometric amounts of base allow for coupling, unless there is only one side to pick from, we could end up with mixed products/not the products we want.  To me, it looks like a 50/50 shot of attack at the alkyne hydrogen.  Please do correct me if I'm wrong, which I frequently am!
          Cheers
               -Zack

One more question: Dont you need to protect the other carbon in acetylene when doing the coupling reaction? So you dont get acetylene substitued on both carbons.

No, you don`t have to. As I have written, by using one equivalent of a base, acetylene can be gradually alkylated in the great yields. Look at my method.

[zsinger]

Sorry last one…..Hunsdieker is messy and not a fun nor neat reaction, as you are dealing with elemental Bromine (you do not want to find out how toxic…..trust me).  Avoid at all costs.

[408]

EtBr+Zn--> Butane
Butane-(radical halogenation& isomer separation)-->1-chloro butane (or start with methanol and do successive SOCl2, Mg, CH2O treatments till you get butanol and 1-chlorobutane lol)

BnOH-->BnCl
BnCl--(1.grig, 2. CH2O)-->Ph-CH2-CH2-OH--(SOCl2)-> Ph-CH2CH2-Cl

PhCH2CH2Cl--(Mg)-->PhCH2CH2MgCl--(Acetaldehyde)-->PhCH2CH2C(OH)CH3--(ox)-->PhCH2CH2C(O)CH3

BuCl-(Mg)->BuMgCl--(PhCH2CH2C(O)CH3)--> product.

But really, lots of different routes.  Above reactions are all just intro ochem to keep things simple.

[kriggy]

I am somewhat sure that this is not the 100% correct answer……while you are correct that stoichiometric amounts of base allow for coupling,
unless there is only one side to pick from, we could end up with mixed products/not the products we want.
 To me, it looks like a 50/50 shot of attack at the alkyne hydrogen.  Please do correct me if I'm wrong, which I frequently am!
          Cheers
               -Zack

Yes thast exactly what I was thinking. From my limited N-alkylation experience its exactly like that. Even with 1:1 ratio, we got mixture of mono, dialkylated (2 equivalent nitrogens)
and nonalkylated. Not to mention that they are pain to separate.
I guess its fine at paper but..

[orgopete]

This looks like an acetoacetate problem. Has this been taught yet? If so, I'd use it. If so, I think this could be a five or six step synthesis (depending on how you are counting).
[Edit, nope. I missed the requirement for two carbons or less for every step. It would be be longer than my earlier prediction.]