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Synthesis 1987; 1987(10): 951-953
DOI: 10.1055/s-1987-28138
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2-Methoxy-2H-chromene aus 2-Bromphenolen und 3-Trimethylsilyloxyacroleinen

Friedrich-Wilhelm Ulrich* , Eberhard Breitmaier
  • *Institut für Organische Chemie und Biochemie der Universität Bonn, Gerhard-Domagk-Str 1, D-5300 Bonn, West Germany
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Publication Date:
12 September 2002 (online)

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2-Methoxy-2H-chromenes from 2-Bromophenols and 3-Trimethylsilyloxyacroleins The preparation of 2-methoxy-2H-chromenes 6 from 2-bromophenols 1 and 3-trimethylsilyloxyacroleins 4 as C3 anellation reagents is described. Heterocyclization involves C-C linkage of ortho-lithiated 2-phenoxytetrahydropyrans 3 with 3-trimethylsilyloxyacroleins 4, followed by cyclization of the intermediate γ-hydroxysilylenolethers as lithium alkoxides 5, induced by hydrogen chloride in methanol. o-Hydroxycinnamic aldehydes 7 are isolated upon workup with trifluoroacetic acid instead of hydrogen chloride.