[Ak]

hi,
i have to synthesize an alcohol from an alkyne.  Wut i came up with is to make it into a alkene using H2 and a Lindlar catalyst.  Then treating the alkene with BH3 and then H202, OH-...so basically hydroboration/oxidation

My question is, is this mechanism possible and secondly is there an easier way?

[InTruDeR]

Easier way: Alkyne +H2 -> Alchene  +HCl-> R-Cl  .. then you add hidrolise...
And you get your alcohol.
Sorry for my english.

[macman104]

Yes that mechanism is possible.  Your method of hydrogenation followed by hydroboration/oxidation is probably the easiest way, I'm not sure why InTruDeR thinks that method is shorter/simpler...

[kiwi]

Your method is fine, but another approach would be catalytic anti-Markovnikov hydration of the alkyne (eg. Org Lett (2006) 5853-5856; DOI: 10.1021/ol062455k) then borohydride reduction of the resulting aldehyde.

[Ak]

Thanks a lot guys

[movies]

Your method is fine, but another approach would be catalytic anti-Markovnikov hydration of the alkyne (eg. Org Lett (2006) 5853-5856; DOI: 10.1021/ol062455k) then borohydride reduction of the resulting aldehyde.

You can get the isomeric alcohol by hydrating the alkyne in the presence of mercury(II) to give a methyl ketone.  Then sodium borohydride reduction would give the secondary alcohol.