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  • Title: Vilsmeier-Haack reaction of 1-cyclopropyl-2-arylethanones.
    Author: Tang XY, Shi M.
    Journal: J Org Chem; 2008 Nov 07; 73(21):8317-20. PubMed ID: 18817448.
    Abstract:
    A convenient and efficient method to synthesize 3-(2-chloroethyl)-5-aryl-4H-pyran-4-ones 2 and 2-chloro-3-(2-chloroethyl)-1-naphthaldehydes 3 in moderate to good yields was developed via the Vilsmeier-Haack reaction of readily available 1-cyclopropyl-2-arylethanones 1 at different temperature. This reaction proceeds via sequential enolization, ring opening, haloformylation, and intramolecular nucleophilic cyclization or Friedel-Crafts alkylation reactions to produce 2 or 3.
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