A practical synthesis of benzyl esters and related derivatives

Tetrahedron Letters

Volumn 39, Issue 40, 1998, Pages 7301-7304

  Fauré Tromeur, Mélanie ^a   Zard, Samir Z ^a,b  

^a CNRS   (France)

^b LABORATOIRE DE SYNTHÈSE ORGANIQUE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

BENZYL DERIVATIVE;

ARTICLE; CONFORMATIONAL TRANSITION; STRUCTURE ANALYSIS; SYNTHESIS;

EID: 0032191485     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(98)01563-9     Document Type: Article

References (19)

1. 1. Kocienski, P. J. Protecting Groups, Georg Thieme Verlag Stuttgart, New York (1994).
2. 2. Bergmann, M.; Zervas, L. ; Salzmann, L. Ber. 1933, 66, 1288-1290.
3. 3. Klemm, H. P.; Hintze, U.; Gercken, G. J. Chromatog. 1973, 75, 19-27.
4. 4. Vowinkel, E. Chem. Ber. 1967, 100, 16-22.
5. 5. (a) Williams, K.; Halpern, B. Synthesis 1974, 727-728.
6. (b) idem. Aust. J. Chem. 1975, 28, 2065-2068.
7. 6. Kokotos, G.; Chiou, A. Synthesis 1997, 168-170. The Lewis acid may not be essential, see for example: Thierry, J.; Yue, C.; Potier, P. Tetrahedron lett. 1998, 39, 1557-1560.
8. 6. Kokotos, G.; Chiou, A. Synthesis 1997, 168-170. The Lewis acid may not be essential, see for example: Thierry, J.; Yue, C.; Potier, P. Tetrahedron lett. 1998, 39, 1557-1560.
9. 7. For a review, see: Zard, S. Z. Angew. Chem. Int. Ed. Engl. 1997, 36, 672-685.
10. 8. Boivin, J.; Henriet, E. B.; Zard, S. Z. J. Am. Chem. Soc. 1994, 116, 9739-9740.
11. 9. Altenbach, H.-J. in Comprehensive Organic Synthesis, Trost, B. M.; Fleming, I., Eds; Pergamon press, New York: 1991; Vol 6, p 829-871.
12. 10. (a) Schönberg, A.; Vargha, L. Chem. Ber. 1930, 63, 178.
13. (b) Villemin, D.; Hachemi, M. Synth. Commun. 1996, 26, 2449-2459.
14. (c) Barton, D. H. R.; Choi, S.-Y. Tetrahedron Lett. 1996, 37, 2695-2698 and references there cited.
15. 11. Benzyl alcohol (100 mmol) was added to sodium hydride (100 mmol, oil dispersion) suspended in anhydrous tetrahydrofuran (150 ml.). After stirring at room temperature for 30 min., carbon disulfide (700 mmol.) was added and the solution stirred for 2 hrs. Propargyl bromide (500 mmol) was then added and the mixture left at room temperature for 3 hrs. The reaction was then quenched with saturated ammonium chloride solution, extracted with dichloromethane, dried over anhydrous sodium sulfate and concentrated in vacuo. The crude product was passed through a silica gel column, eluting with pentane to yield pure O-benzyl-S-propargyl xanthate 1a (1.5 g, 68%).
16. 12. Typical experimental procedure : a solution of the xanthate 1 (0.75 mmol) and the appropriate acid 2 (0.5 mmol) in toluene (4 ml) was heated to reflux for several hrs. The solution was allowed to cool and the crude product was purified by chromatography after evaporation of the solvent.
17. 13. (a) Prhavc, M.; Kobe, J. Tetrahedron lett. 1990, 31, 1925-1928.
18. (b) Huff, L.; Henry, R. A. J. Med. Chem. 1970, 13, 777-778.
19. 14. Ballesteros, P.; Claramunt, R. M. Tetrahedron 1987, 43, 2557-2564.