Linked Life Data

20090989

Source:http://linkedlifedata.com/resource/pubmed/id/20090989

Statements in which the resource exists as a subject.
PredicateObject
rdf:type
lifeskim:mentions
pubmed:issue
3
pubmed:dateCreated
2010-1-21
pubmed:abstractText
5-Hydroxy-1,3-diketones have been synthesised in a facile one-pot reaction from the treatment of acid chlorides with non-substituted ketones and LiHMDS. Subsequent cyclisation to 2,3-dihydro-4H-pyran-4-ones occurs rapidly and in high yield (89-99%) when mediated by anhydrous indium(iii) chloride. A spectroscopic study of the reaction using in situ Fourier transform infrared (FTIR) spectroscopy has shown the reaction to be highly dependent on temperature, metal complex formation and InCl(3) concentration. Since the reaction is deactivated by the precipitation of [InCl(3).(H(2)O)(3)], the concurrent use of a stronger drying agent, such as molecular sieves 4 A or anhydrous MgSO(4), allows the reaction to be successfully carried out at relatively low loadings of InCl(3) (1-10%). In their absence, the optimum reaction conditions were found to be a diketone : InCl(3) ratio of 3 : 1 in toluene, and a reaction temperature of 80 degrees C.
pubmed:language
eng
pubmed:journal
pubmed:citationSubset
IM
pubmed:chemical
pubmed:status
MEDLINE
pubmed:month
Feb
pubmed:issn
1477-0539
pubmed:author
pubmed:issnType
Electronic
pubmed:day
7
pubmed:volume
8
pubmed:owner
NLM
pubmed:authorsComplete
Y
pubmed:pagination
698-705
pubmed:meshHeading
pubmed:year
2010
pubmed:articleTitle
Highly efficient indium(III)-mediated cyclisation of 5-hydroxy-1,3-diketones to 2,3-dihydro-4H-pyran-4-ones; mechanistic insights from in situ Fourier transform infrared spectroscopy.
pubmed:affiliation
School of Chemistry, Monash University, Clayton, Melbourne, Vic 3800, Australia. phil.andrews@sci.monash.edu.au
pubmed:publicationType
Journal Article, Research Support, Non-U.S. Gov't