ORGLIST: Acetylene from methylbutinol

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From: Witek Mozga (mozgaw$##$rocketmail.com)
Date: Tue Jan 09 2001 - 14:32:13 EST


Hi Everybody!

I`m trying to synthesize an acetylene derivative, in which the triple
bond is connected to the aromatic ring. Using the adduct of
acetylene and acetone (methylbutinol) in Heck reaction I have
obtained the product depicted below:

Ar-Br + H-C#C-C(CH3)2-OH -> Ar-C#C-C(CH3)2-OH

# symbolizes triple bond

Could anyone tell me how to reconvert the butinol moiety into
acetylene again? I mean this:

Ar-C#C-C(CH3)2-OH -> Ar-C#C-H + acetone

I heard that you should add an catalytic amount of NaH and distil out
acetone from the mixture along with another solvent (toluene).

Does anybody have experience in this method?
Or maybe you could suggest another way to obtain the acetylene
derivative from methylbutinol?

With Best Regards,

Witek Mozga

mozgaw$##$rocketmail.com
mozga$##$trimen.pl
http://www.trimen.pl
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