Butyllithium reaction with propargyl alcohols

Better intermolecular yields were obtained by switching over to propargylic alcohol a reaction which is already known to work with Grignard reagents The yield was 48 % using ethyllithium, but n-butyllithium and phenyllithium have also been added in 15% and 42% yield, respectively The reaction is catalyzed by 10% copper(I) iodide. Without this catalyst the yields are only about half of the... 

As noted above, alkyne anions are very useful in Sn2 reactions with alkyl halides, and in acyl addition reactions to a carbonyl.46 Alkyl halides and sulfonate esters (tosylates and mesylates primarily) serve as electrophilic substrates for acetylides. A simple example is taken from Kaiser s synthesis of niphatoxin B, in which propargyl alcohol (36) is treated with butyllithium and then the OTHP derivative of 8-bromo-1-octanol to give a 47% yield of 37.48... 

Amino aldehydes can also be condensed with tiiphenylphosphonium ylids in a Wittig olefination reaction.134 Generation of the propargyl alcohol derivative 1.228 allowed conversion of the hydroxyl group to a bromide and then to the triphenyl-phosphonium salt. Treatment with n-butyllithium gave the ylid, which reacted with... 

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