Download PDF
Synfacts 2008(9): 0996-0996  
DOI: 10.1055/s-2008-1078660
Polymer-Supported Synthesis
© Georg Thieme Verlag Stuttgart ˙ New York

Aldol-Type Coupling of Ethyl Diazoacetate with SiO2-TMG

Contributor(s): Yasuhiro Uozumi, Yutaka Matsuura
P. R. Likhar*, S. Roy, M. Roy, M. S. Subhas, M. L. Kantam
Indian Institute of Chemical Technology, Hyderabad, India
Further Information

Publication History

Publication Date:
22 August 2008 (online)

    Permissions and Reprints

Significance

Silica-supported tetramethylguanidine (SiO2-TMG) was prepared by treatment of O-TMS-capped chloropropyl-modified silica 2 with 1,1,3,3-tetramethylguanidine (TMG). The aldol-type reaction of various aldehydes 3 and ethyl di­azoacetate 4 took place in the presence of SiO2-TMG in DMSO to give the corresponding products 5 in 60-95% yield. The SiO2-TMG catalyst was separated from the reaction mixture by simple filtration, and reused five times with no significant loss of activity in the reaction of 4-bromobenz­aldehyde and ethyl diazoacetate.