A simple approach to separate a mixture of homopropargylic and allenic alcohols.
A simple and practical approach to separate homopropargylic alcohol from allenic alcohol has been developed. It involves the formation of an insoluble silver acetylide species between silver nitrate and homopropargylic alcohol in aqueous acetone which can be separated from the allenic alcohol through a simple filtration. The homopropargylic alcohol can subsequently be recovered by hydrolysis with 1 N HCl. This protocol has been applied to the separation of a mixture of chiral homopropargylic and allenic alcohols in excellent yields with retention of absolute stereochemistry.
Fu
Fan
F
Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371, Singapore.
Hoang
Kim Le Mai
Kle M
Loh
Teck-Peng
TP
D000096:Acetone / Q000737:chemistry; D000438:Alcohols / Q000737:chemistry*; D000466:Alkadienes / Q000737:chemistry*; D000440:Butanols / Q000737:chemistry*; D011232:Chemical Precipitation; D005374:Filtration; D006868:Hydrolysis; D015394:Molecular Structure; D012835:Silver Nitrate / Q000737:chemistry
D000438:Alcohols; D000466:Alkadienes; D000440:Butanols; D000096:Acetone; D012835:Silver Nitrate