Abstract
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.
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