The aqueous trimethylamine mediated Baylis-Hillman reaction

Synthetic Communications

Volumn 30, Issue 11, 2000, Pages 2061-2069

  Basavaiah, Deevi ^a   Krishnamacharyulu, Marimganti ^a   Rao, Anumolu Jaganmohan ^a  

^a UNIVERSITY OF HYDERABAD   (India)

Author keywords

[No Author keywords available]

Indexed keywords

ACRYLIC ACID DERIVATIVE; ALDEHYDE; TRIMETHYLAMINE;

AQUEOUS SOLUTION; ARTICLE; CATALYST; CHEMICAL BOND; CHEMICAL REACTION; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0034026611     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397910008087256     Document Type: Article

References (26)

1. a) Basavaiah, D.; Dharma Rao, P.; Suguna Hyma, R. Tetrahedron, 1996, 52, 8001.
2. b) Ciganek, E. Organic Reactions. 1997, vol. 51, pp 201-350 (Paquette, L.A., Editor), John Wiley & Sons, New York.
3. Drewes, S.E.; Roos, G.H.P. Tetrahedron, 1988, 44, 4653.
4. a) Basavaiah, D.; Bakthadoss, M.; Pandiaraju, S. Chem. Commun., 1998, 1639.
5. b) Basavaiah, D.; Krishnamacharyulu, M.; Suguna Hyma, R., Pandiaraju, S. Tetrahedron Lett., 1997, 38, 2141.
6. Basavaiah, D.; Krishnamacharyulu, M.; Suguna Hyma, R.; Sarma, P.K.S.; Kumaragurubaran, N. J. Org. Chem., 1999, 64, 1197.
7. Basavaiah, D.; Sarma, P.K.S.; Bhavani, A.K.D. J. Chem. Soc., Chem. Commun., 1994, 1091.
8. Rezgui, F.; El Gaied, M.M. Tetrahedron Lett., 1998, 39, 5965.
9. Kataoka, T.; Iwama, T.; Tsujiyama, S. Chem. Commun., 1998, 197.
10. Barrett, A.G.M.; Cook, A.S.; Kamimura, A. Chem. Commun., 1998, 2533.
11. Hayase, T.; Shibata, T.; Soai, K.; Wakatsuki, Y. Chem. Commun., 1998, 1271.
12. Nakagawa, K.; Makino, M.; Kita, Y. Eur. Patent Appl. EP 669,312 (1995); Chem. Abstr., 1995, 123, 285218v.
13. Nakagawa, K.; Makino, M.; Kita, Y. Eur. Patent Appl. EP 669,312 (1995); Chem. Abstr., 1995, 123, 285218v.
14. 3 for 3 days in 94% yield. See: Bode, M.L.; Kaye, P.T. J. Chem. Soc., Perkin Trans. 1, 1993, 1809.
15. Preparation of molecule 1 (Representative procedure): A mixture of pyridine-2-carboxaldehyde (10 mmol, 1.071 g), methyl acrylate (30 mmol, 2.583 g) and aqueous trimethylamine (30% w/v) (12 mmol, 2.36 mL) was heated at 60°C for 4 hours. The reaction mixture was then cooled to room temperature, layers separated and the aqueous layer was extracted with ether (3 × 10 mL). The combined organic layer was dried over anhydrous sodium sulfate, concentrated and silica gel column chromatography (5% ethyl acetate in hexanes) of the crude product thus obtained, has provided 1.196 g (62%) of methyl 3-hydroxy-2-methylene-3-(pyrid-2-yl)propanoate (1) as a colorless oil.
16. a) Masuyama, Y.; Nimura, Y.; Kurusu, Y. Tetrahedron Lett., 1991, 32, 225.
17. b) Drewes, S.E.; Loizou, G.; Roos, G.H.P. Synth. Commun., 1987, 17, 291.
18. Preparation of molecule 14: A mixture of cyclohex-2-en-l-one (20 mmol, 1.923 g) and aqueous trimethylamine (30% w/v) (24 mmol, 4.72 mL) was heated at 60°C for 6 hours. Usual work up followed by silica gel column chromatography (10% ethyl acetate in hexanes) has provided 0.680 g (35%) of 14 as pale yellow oil.
19. 13C NMR) are reported in the literature Spectral data of these molecules are agreement with the literature data. For molecule 1, see: Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr., 1989, 403. For molecule 2, see: ref 8. For molecule 4, see: ref: 15. For molecules 7 and 9, see: Fort, Y.; Berthe, M.C.; Caubere, P. Tetrahedron, 1992, 48, 6371. For molecule 10, see: ref: 10b. For molecule 11, see: ref: 16. For molecule 13, see: Novarro, C.; Castaing, M.D-; Colombani, D.; Maillard, B. Synth. Commun., 1993, 23, 1025. For molecule 14, see: Mubarak, M.S.; Pagel, M.; Marcus, L.M.; Peters, D.G. J. Org. Chem., 1998, 63, 1319.
20. 13C NMR) are reported in the literature Spectral data of these molecules are agreement with the literature data. For molecule 1, see: Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr., 1989, 403. For molecule 2, see: ref 8. For molecule 4, see: ref: 15. For molecules 7 and 9, see: Fort, Y.; Berthe, M.C.; Caubere, P. Tetrahedron, 1992, 48, 6371. For molecule 10, see: ref: 10b. For molecule 11, see: ref: 16. For molecule 13, see: Novarro, C.; Castaing, M.D-; Colombani, D.; Maillard, B. Synth. Commun., 1993, 23, 1025. For molecule 14, see: Mubarak, M.S.; Pagel, M.; Marcus, L.M.; Peters, D.G. J. Org. Chem., 1998, 63, 1319.
21. 13C NMR) are reported in the literature Spectral data of these molecules are agreement with the literature data. For molecule 1, see: Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr., 1989, 403. For molecule 2, see: ref 8. For molecule 4, see: ref: 15. For molecules 7 and 9, see: Fort, Y.; Berthe, M.C.; Caubere, P. Tetrahedron, 1992, 48, 6371. For molecule 10, see: ref: 10b. For molecule 11, see: ref: 16. For molecule 13, see: Novarro, C.; Castaing, M.D-; Colombani, D.; Maillard, B. Synth. Commun., 1993, 23, 1025. For molecule 14, see: Mubarak, M.S.; Pagel, M.; Marcus, L.M.; Peters, D.G. J. Org. Chem., 1998, 63, 1319.
22. 13C NMR) are reported in the literature Spectral data of these molecules are agreement with the literature data. For molecule 1, see: Foucaud, A.; El Guemmout, F. Bull. Soc. Chim. Fr., 1989, 403. For molecule 2, see: ref 8. For molecule 4, see: ref: 15. For molecules 7 and 9, see: Fort, Y.; Berthe, M.C.; Caubere, P. Tetrahedron, 1992, 48, 6371. For molecule 10, see: ref: 10b. For molecule 11, see: ref: 16. For molecule 13, see: Novarro, C.; Castaing, M.D-; Colombani, D.; Maillard, B. Synth. Commun., 1993, 23, 1025. For molecule 14, see: Mubarak, M.S.; Pagel, M.; Marcus, L.M.; Peters, D.G. J. Org. Chem., 1998, 63, 1319.
23. 2 74.66 (74.97) 8.34 (8.39) - # Elemental analysis is furnished for either unknown molecules or the known molecules whose spectral data is not fully reported in the literature. @ Recorded on a Perkin-Elmer 240C-CHN analyzer.
24. 16 65-70°C/1mm); Compound 12: b.p.: 80°C/0.5mm; Compound 13: b.p.: 76°C/0.5mm.
25. Foucaud, A.; Rouille, E. Synthesis, 1990, 787.
26. Villieras, J.; Rambaud, M. Synthesis, 1982, 11, 924.