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Bulletin of the Korean Chemical Society (BKCS)

ISSN 0253-2964(Print)
ISSN 1229-5949(Online)
Volume 22, Number 12
BKCSDE 22(12)
December 20, 2001 

A Facile Preparation of 2-(2-Hydroxyethyl)homoallenylsilanes Using In Situ Generated Homoallenylindium Reagent
Phil Ho Lee, Keukchan Bang, Hyosoon Ahn, Kooyeon Lee
4-Bromo-3-[(trimethylsilyl)methyl]-1,2-butadiene, Indium, Homoallenylation, 2-(2-Hydroxyethyl) homoallenylsilane.
In situ generated homoallenylindium reagents derived from the reaction of indium with 4-bromo-3-[(tri-methylsilyl) methyl]-1,2-butadiene reacted with a variety of aldehydes in DMF to produce 2-(2-hydroxy-ethyl) homoallenylsilanes at room temperature in good to excellent yields. 2- or 3-Hydroxybenzaldehyde that contains labile hydrogen was reacted with homoallenylindium reagent to provide the homoallenylsilanes. In the case of 4-formylbenzoic acid, the desired compound was produced in 88% yield. 4-Bromo-3-[(trimethyl-silyl) methyl]-1,2-butadiene was prepared from monoacetylation and mesylation of 2-butyn-1,4-diol, addition of trimethylsilylmethyl anion, saponification and mesylation followed by Finkelstein reaction.
1385 - 1389
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