Large scale synthesis of acetylene dicarboxaldehyde mono and diacetal

Tetrahedron Letters

Volumn 45, Issue 9, 2004, Pages 1829-1832

  Akué Gédu, Rufine ^a   Rigo, Benoît ^a  

^a Ecole des Hautes Etudes d'Ingenieur   (France)

Author keywords

2,5 Dimethoxy 2,5 dihydrofuran; Acetylene dicarboxaldehyde; Atom economy

Indexed keywords

2,5 DIMETHOXY 2,5 FURAN; ACETAL DERIVATIVE; ACETYLENE DERIVATIVE; ACETYLENE DICARBOXALDEHYDE; ALDEHYDE DERIVATIVE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; ATOM; ECONOMIC ASPECT; SCALE UP; SYNTHESIS;

EID: 1242316321     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2004.01.022     Document Type: Article

References (29)

1. Gorgues A. Janssen Chim. Acta. 4:1986;21-26.
2. Gorgues A., Le Coq A. Tetrahedron Lett. 20:1979;4829-4832.
3. Henkel K., Weygand F. Chem. Ber. 76B:1943;812-821.
4. Ramanaiah K.C.V., Stevens E.D., Trudell M.L., Pagoria P.F. J. Heterocyclic Chem. 37:2000;1597-1602.
5. Frère P., Belyasmine A., Gouriou Y., Jubault M., Gorgues A., Duguay G., Wood S., Reynolds C.D., Bryce M.R. Bull. Soc. Chim. Fr. 132:1995;975-984.
6. Gorgues A., Simon A., Le Coq A., Hercouet A., Corre F. Tetrahedron. 42:1986;351-370.
7. Gorgues A., Stephan D., Belyasmine A., Khanous A., Le Coq A. Tetrahedron. 46:1990;2817-2826.
8. Gorgues A., Le Coq A. Chem. Commun. 1979;767-768.
9. Stephan D., Gorgues A., Belyasmine A., Le Coq A. Chem. Commun. 1988;263-264.
10. Blanco L., Bloch R., Bugnet E., Deloisy S. Tetrahedron Lett. 41:2000;7875-7878.
11. Barrett A.G.M., Hamprecht D., Ohkubo M. J. Org. Chem. 62:1997;9376-9378.
12. Le Coq A., Gorgues A. Org. Synth. Coll. 6:1988;954-957.
13. Montaña A.M., Fernandez D., Pagès R., Filippou A.C., Kociok-Köhn G. Tetrahedron. 56:2000;425-439.
14. 3,3-Diethoxy-1-propyne (Scheme 1): 329 €/25 g (Lancaster); 3a: 75 €/1 g (Acros); 2a: 78 €/1 g (Acros); 4: 191 €/1000 g (Alfa Aesar).
15. 2,5-dimethoxy-2,5-dihydrofuran ( 4 ) is a commercial synthon, which is very versatile: Kass N.C., Limborg F., Fakstorp J. Acta Chem. Scand. 2:1948;109-115.
16. Baussanne I., Chiaroni A., Riche C., Royer J., Husson H.-.P. Tetrahedron Lett. 35:1994;3931-3934.
17. Merz A., Meyer T. Synthesis. 1:1999;94-99.
18. Malanga C., Mannucci S. Tetrahedron Lett. 42:2001;2023-2025.
19. Katritzky A.R., Metha S., He H.-Y. J. Org. Chem. 66:2001;148-152.
20. Gagnaire D., Vottero P. Bull. Soc. Chim. Fr. 1963;2779-2784.
21. 4.
22. Brecker L., Kreiser W., Ernst L., Hopf H. Collect. Czech. Chem. Commun. 64:1999;1154-1158.
23. Utilization of trimethyl orthoformate as water scavenger during methanolysis of 2,5-dimethyl-2,5-dihydrofuran has been described: BASF A.-G. Ger. Offen. 1994, 4.223.889.
24. Chem. Abstr. 120:1994;216711.
25. Product 6b is difficult to purify but remaining impurities are removed during the treatment of the next step.
26. 1g.
27. Acid hydrolysis of acetal 3a is very difficult: Wohl A., Bernreuter E. Ann. Chem. 481:1930;1-29.
28. Gorgues A. Bull. Soc. Chim. Fr. 1974;529-530.
29. 1g This compound remains unaltered for years when kept at -40°C.