o-Formylation of electron-rich phenols with dichloromethyl methyl ether and TiCl4

Tetrahedron Letters

Volumn 44, Issue 27, 2003, Pages 4961-4963

  García, Oscar ^a   Nicolás, Ernesto ^a   Albericio, Fernando ^a  

^a UNIVERSITY OF BARCELONA   (Spain)

Author keywords

Benzofuran; Benzopyran; Handle; Linker; Protecting group; Solid phase

Indexed keywords

(8 FORMYL 3,4 DIHYDRO 2 METHYL 5,6,7 TRIMETHOXY 2H 1 BENZOPYRAN 2 YL)ACETIC ACID; 2 FORMYL 3,4,5 TRIMETHOXYPHENOL; 2 FORMYL 3,5 DIMETHOXYPHENOL; 2 FORMYL 3,5,6 TRIMETHYLPHENOL; 2,3 DIHYDRO 2,2 DIMETHYL 4,5,6 TRIMETHOXYBENZOFURAN 7 CARBALDEHYDE; 4 FORMYL 3,5,6 TRIMETHYLPHENOL; ACETIC ACID DERIVATIVE; ALDEHYDE DERIVATIVE; DICHLOROMETHYLMETHYL ETHER; ETHER DERIVATIVE; PHENOL DERIVATIVE; TITANIUM DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL STRUCTURE; CHROMATOGRAPHY; HYPOTHESIS; LITHIATION; PURIFICATION; QUANTITATIVE ANALYSIS; REACTION ANALYSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; TECHNIQUE; VILSMEIER HAACK REACTION;

EID: 0037505294     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(03)01168-7     Document Type: Article

References (10)

1. Lloyd-Williams P., Albericio F., Giralt E. Chemical Approaches to the Synthesis of Peptides and Proteins. 1997;CRC, Boca Raton, FL, Solid-Phase Synthesis. A Practical Guide; Kates, S. A.; Albericio, F., Eds.; Marcel Dekker: New York, 2000.
2. Albericio F., Giralt E. Goodman M., Felix A., Moroder L., Toniolo C. Houben-Weyl. Methods of Organic Chemistry. Vol. E 22. Synthesis of Peptides and Peptidomimetics. 2001;685-709 Georg Thieme, Stuttgart.
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6. Gross H., Rieche A., Mattey G. Chem. Ber. 96:1963;308-319.
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8. Landi J.J., Ramig K. Synth. Commun. 21:1991;167-171.
9. The reaction could take place through the following mechanism
10. Solladié et al. have also reported excellent yields for the formylation of pentamethylchromans, systems similar to 5 (see Ref. 3).