The synthesis of substituted phenols from pyranone precursors

• Published in: Tetrahedron Vol. 65; no. 39; pp. 8165 - 8170
• Main Authors: Marshall, Laura J., Cable, Karl M., Botting, Nigel P.
• Format: Journal Article
• Language: English
• Published: OXFORD Elsevier Ltd 26.09.2009; Elsevier
• Subjects: 2,6-Dimethylpyranone; Chelidonic acid; Chemistry; Chemistry, Organic; Exact sciences and technology; Heterocyclic compounds; Heterocyclic compounds with o, s, se, te hetero atom and condensed derivatives; Isotopes; Maltol; Noncondensed benzenic compounds; Organic chemistry; Phenol; Physical Sciences; Preparations and properties; Pronucleophile; Pyranone; Science & Technology; Phenol; Pyranone; Maltol; Pronucleophile; 2,6-Dimethylpyranone; Isotopes; Chelidonic acid; ACID; QUANTIFICATION; ISOFLAVONES; ETHERS; REAKTIONEN MIT PYRYLIUMSALZEN; LIGNANS; SPECTROMETRY; Pyran derivatives; Microwave; Thermal reaction; Pyranone derivatives; Oxygen heterocycle; Ketone; Benzylic compound; Diester; Phenols; Chemical synthesis; Solvent
• ISSN: 0040-4020; 1464-5416
• DOI: 10.1016/j.tet.2009.07.083

The syntheses of various substituted phenols from pyranone precursors, namely 4H-pyran-4-one, 3-(benzyloxy)-2-methyl-4H-pyran-4-one (benzyl-maltol), 2,6-dimethyl-4H-pyran-4-one and diethyl 4-oxo-4H-pyran-2,6-dicarboxylate (diethyl chelidonate) are presented. A variety of pronucleophiles were used in combination with tert-butanol as solvent and potassium tert-butoxide as base, using conventional heating methods and microwave conditions. [Display omitted]