A simple approach to separate a mixture of homopropargylic and allenic alcohols

Fan Fu; Kim Le Mai Hoang; Teck Peng Loh

doi:10.1021/ol801087s

A simple approach to separate a mixture of homopropargylic and allenic alcohols

Fan Fu^*, Kim Le Mai Hoang, Teck Peng Loh

^*Corresponding author for this work

Nanyang Technological University

Research output: Contribution to journal › Article › peer-review

9 Citations (Scopus)

Abstract

(Chemical Equation Presented) 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.

Original language	English
Pages (from-to)	3437-3439
Number of pages	3
Journal	Organic Letters
Volume	10
Issue number	16
DOIs	https://doi.org/10.1021/ol801087s
Publication status	Published - 2008
Externally published	Yes

ASJC Scopus Subject Areas

Biochemistry
Physical and Theoretical Chemistry
Organic Chemistry

Access to Document

10.1021/ol801087s

Cite this

@article{46aa07d8b6fb413d89339bac3e6f630e,

title = "A simple approach to separate a mixture of homopropargylic and allenic alcohols",

abstract = "(Chemical Equation Presented) 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.",

author = "Fan Fu and Hoang, {Kim Le Mai} and Loh, {Teck Peng}",

year = "2008",

doi = "10.1021/ol801087s",

language = "English",

volume = "10",

pages = "3437--3439",

journal = "Organic Letters",

issn = "1523-7060",

publisher = "American Chemical Society",

number = "16",

}

TY - JOUR

T1 - A simple approach to separate a mixture of homopropargylic and allenic alcohols

AU - Fu, Fan

AU - Hoang, Kim Le Mai

AU - Loh, Teck Peng

PY - 2008

Y1 - 2008

N2 - (Chemical Equation Presented) 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.

AB - (Chemical Equation Presented) 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.

UR - http://www.scopus.com/inward/record.url?scp=54049100822&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=54049100822&partnerID=8YFLogxK

U2 - 10.1021/ol801087s

DO - 10.1021/ol801087s

M3 - Article

C2 - 18630915

AN - SCOPUS:54049100822

SN - 1523-7060

VL - 10

SP - 3437

EP - 3439

JO - Organic Letters

JF - Organic Letters

IS - 16

ER -

A simple approach to separate a mixture of homopropargylic and allenic alcohols

Abstract

ASJC Scopus Subject Areas

Access to Document

Other files and links

Fingerprint

Cite this