[Meter]

Hi all.

I'm a little stumped as to what reagents I need for this step. It's entirely possible that several different reactions are required.

My initial thought was to do some type of "alkylation" to the terminal alkyne using NaNH₂ with an appropriate compound, but it seems that those only work for haloalkanes? Anyway I would need a way to add the hydroxyl group as well. Can I get a hint? 

[Meter]

I think I figured it out.

Deprotonate the terminal alkyne with sodium amide, then use the resulting nucleophile for nucleophilic acyl substitution on an appropriate acyl halide, after which it is reduced using something like sodium borohydride.

[sjb]

Is addition to an acyl halide then reduction necessary? Can you use something that corresponds to the reduced acyl halide first?

[Meter]

Is addition to an acyl halide then reduction necessary? Can you use something that corresponds to the reduced acyl halide first?

Just the equivalent alcohol?

[Babcock_Hall]

An alcohol does not have a good leaving group.

[Meter]

An alcohol does not have a good leaving group.

If it's attached directly to a halogen, then the halogen would be the leaving group, no?

[Meter]

I was thinking either of these two.

[Babcock_Hall]

I would question whether or not the structure on the righthand side is a stable molecule.  I am not 100% certain.  There are also some questions in my mind about side reactions, but this particular exercise may not be concerned about such things.

[Meter]

I would question whether or not the structure on the righthand side is a stable molecule.  I am not 100% certain.  There are also some questions in my mind about side reactions, but this particular exercise may not be concerned about such things.

No, it was one of those "synthesize A from B using any reagents and starting materials" type questions. I think the acyl halide would be more stable through resonance, no?

[rolnor]

What functional group will give an alcohol directly after addition of a carbon nucleophile?

[Meter]

What functional group will give an alcohol directly after addition of a carbon nucleophile?

Aldehyde/ketones ?

[Babcock_Hall]

Meter, I agree with Rolnor.  My earlier comment was prompted by the presence of an additional functional group, which means that one should consider the possibility of side reactions.  However, I don't have any special knowledge about this particular addition.

[rolnor]

Yes, with a aldehyde you will save one step.

[Meter]

Yes, with a aldehyde you will save one step.

Good to know for the future. Thanks.