A mild synthesis of substituted furans from -γ-hydroxy-α,β-unsaturated ketones

Tetrahedron Letters

Volumn 37, Issue 34, 1996, Pages 6065-6068

  Sammond, Douglas M ^a   Sammakia, Tarek ^a  

^a UNIVERSITY OF COLORADO   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

FURAN DERIVATIVE; KETONE DERIVATIVE;

ARTICLE; CATALYSIS; DEHYDRATION; PHOTOCHEMISTRY; REACTION ANALYSIS; SYNTHESIS;

EID: 0030593587     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01316-0     Document Type: Article

References (33)

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25. 8 Professor Fred West (University of Utah) has independently discovered and utilized this method in the synthesis of a furan containing substrate. We thank Professor West for disclosing his results prior to publication.
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28. For a recent review, see: McClinton, M. A. Aldrichimica Acta 1995, 28, 31-36. Hydrogen fluoride in acetonitrile can also be utilized for the deprotection and cyclization, however, TREAT is equally effective and milder.
29. 10 These substrates were prepared according to the following scheme: (equation presented)
30. 4, and concentrated under reduced pressure. The product was purified by flash chromatography (hexanes / ethyl acetate) to provide the pure furan in the yield indicated in the table.
31. 13C, and IR).
32. 4, and concentrated under reduced pressure. The crude reaction product was then dissolved in chloroform (3 mL) and placed in a quartz tube. The tube was placed approximately 1 inch from a low pressure mercury vapor lamp, and the solution was irradiated for 20 minutes. The reaction was concentrated under reduced pressure and the product was purified by flash chromatography (hexanes / ethyl acetate) to provide the pure furan in the yield indicated in the table.
33. 15 This substrate was prepared according to the following scheme: (equation presented)