A novel and convenient synthesis of 3-methylfuran-2(5H)-one

Synthesis

Volumn , Issue 3, 1997, Pages 290-292

  Nefkens, Gerard H L ^a   Thuring, Jan Willem J F ^a   Zwanenburg, Binne ^a  

^a RADBOUD UNIVERSITY NIJMEGEN   (Netherlands)

Author keywords

reduction and lactone formation; regioselective ring opening; unsymmetrical cyclic anhydride

Indexed keywords

4 METHYLFURAN 2(5H) ONE; FURAN DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0030983557     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-1180     Document Type: Article

References (18)

1. Hauck, C.; Müller, S.; Schildknecht, H. J. Plant Physiol. 1992, 139, 474.
2. Müller, S.; Hauck, C.; Schildknecht, H. J. Plant Growth Regul. 1992, 11, 77.
3. Siame, B. A.; Weerasuriya, Y.; Wood, K.; Ejeta, G.; Butler, L. G. J. Agric. Food Chem. 1993, 41, 1486.
4. Butler, L. G. ACS Symposium Series 1995, 582, 158.
5. Thuring, J. W. J. F.; Bitter, H.H.; de Kok, M. M. K.; Nefkens, G. H. L.; van Riel, A. M. D. A.; Zwanenburg, B., submitted for publication in J. Agric. Food Chem.
6. Mangnus E. M.; van Vliet, L. A.; Vandenput, D. A. L.; Zwanenburg, B. J. Agric. Food Chem. 1992, 40, 1222.
7. Mangnus E. M.; Dommerholt, F. J.; de Jong, R. L. P.; Zwanenburg, B. J. Agric. Food Chem. 1992, 40, 1230.
8. MacAlpine, G. A.; Raphael, R. A.; Shaw, A.; Taylor, A.W.; Wild, H. J. J. Chem. Soc., Perkin Trans. 1 1976, 410.
9. Johnson, A. W.; Gowda, G.; Hassanali, A.; Knox, J.; Monaco, S.; Razawi, Z.; Roseberry, G. J. Chem. Soc. Perkin Trans. 1 1981, 1734.
10. Franck-Neumann, M.; Berger, C. Bull. Soc. Chim. Fr. 1968, 35, 4067.
11. Mangnus, E. M.; Zwanenburg, B. Synth. Commun. 1992, 22, 783.
12. Näsman, J.H. Org. Synth. 1989, 68, 162.
13. Cruz-Almanza, R.; Padilla Higareda, F. Synth. Commun. 1991, 21, 1097 and refs. cited therein.
14. Jefford, C. W.; Sledeski, A. W.; Rossier, J. C.; Boukouvalas, J. Tetrahedron Lett. 1990, 31, 5741 and refs. cited therein.
15. Alternative convenient procedures involve the use of α-methyl-γ-butyrolactone (ref 13) or α-methylene-γ-butyrolactonc (ref 12), which are very expensive starting materials and difficult to prepare.
16. Kayser, M. M.; Breau, L.; Eliev, S.; Morand, P.; Ip, H. S. Can. J. Chem. 1986, 64, 104.
17. For a typical example see: Minami, M.; Kijima, S. Chem. Pharm. Bull. 1979, 27, 816.
18. Kayser, M. M.; Morand, P. Can. J. Chem. 1980, 58, 2484.