Abstract
Successive one-pot reactions of monolithiated N,N-diethylprop-2-yn-1-amine with 2-(ethenyloxy)ethyl isothiocyanate and 2-(bromomethyl)-1,3-dioxolane afforded 5-[(1,3-dioxolan-2-ylmethyl)sulfanyl]-1[2-(ethenyloxy)ethyl]-N,N-diethyl-1H-pyrrol-2-amine in 91% yield. In the system t-BuOK–DMSO at room temperature (1 h), the product was converted to 1-[2-(ethenyloxy)ethyl]-N,N-diethyl-5-{[2-(2-hydroxyethoxy)ethenyl]sulfanyl}-1H-pyrrol-2-amine (yield 68%) instead of expected 1-vinyl derivative.
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