Xylitol
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Alkylation of terminal alkyne on alcohol
If I have a tertiary acetylenic alcohol and I want to attach an alkyl group to the end of the terminal acetylene, can I use this process or will it
not work if R is an alcohol?
http://www.mhhe.com/physsci/chemistry/carey/student/olc/graphics/carey04oc/ref/ch09preparationofalkynes.html
Is there another way to make this, or does the alcohol have to be made from scratch?
Another way to make from scratch, but chemicals are expensive and it doesn't seem easy:
http://pubs.acs.org/doi/abs/10.1021/jo00116a051
Maybe it could also be made with a grignard, but still, the materials are very expensive. Any ideas?
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CuReUS
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Please give more info about the compound you want to synthesis instead of giving references.Maybe you wouldn't even need to make the alcohol
beforehand.For example: suppose you wanted to make pent-3-yne-1-ol,you could just react propyne with oxirane in the presence of NaNH2.
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Metacelsus
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Sodium amide will deprotonate the alcohol before the terminal alkyne. I agree with CuReUS that more information would be helpful. Depending on the
structure, you could use a ketone and a different terminal alkyne anion. (Example: acetylene + sodium amide + acetone -> 2-methyl-but-3-yn-2-ol)
[Edited on 6-4-2016 by Metacelsus]
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