One-step transformation of 2- or 3-(1-hydroxyalkyl) -2,3-dihydrobenzofurans to the acylbenzofurans with N-bromosuccinimide

Heterocycles

Volumn 45, Issue 9, 1997, Pages 1657-1661

  Suzuki, Hideaki ^a   Tsutsui, Hideyuki ^a   Kano, Atsuyuki ^a   Katoh, Satoru ^a   Morita, Tadashi ^a   Matsuda, Kiyoshi ^a   Iibuchi, Norihiro ^a   Ogawa, Masashi ^a  

^a Tobishi Pharmaceutical Co Ltd   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0037528613     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-7863     Document Type: Article

References (12)

1. a) S. Hanessian, D. H.-c. Wong, and M. Therien, Synthesis, 1981, 394;
2. b) T. Mukaiyama, M. Tsunoda, and K. Saigo, Chem. Lett., 1975, 691;
3. c) G. A. Hiegel and M. Nalbandy, Synth. Commun., 1992, 22, 1589.
4. H. B. Henbest, J. Chem. Soc., 1951, 1074.
5. We confirmed that the simple 5-bromo-2,3-dihydrobenzofuran was converted to 5-bromobenzofuran in 88% yield using NBS under free radical conditions without a base. (Figure Presented)
6. General procedure for the preparation of substrates having 2-hydroxyalkyl group: H. Sato, T. Dan, E. Onuma, H. Tanaka, B. Aoki, and H. Koga, Chem. Pharm. Bull., 1991, 39, 1760.
7. 3-hydroxyalkylated benzofurans: a) D. L. Boger and J. A. McKie, J. Org. Chem., 1995, 60, 1271;
8. b) T. Nagashima and D. P. Curran, Synlett, 1995, 330.
9. 4), and concentrated in vacua. The residue was purified by column chromatography on silica gel (n-hexane-EtOAc, 10:1) to give pure 8 (80%).
10. A diastereomeric mixture was used for the reaction. The ratio was not determind.
11. a) Y. Goldberg, C. Bensimon, and H. Alper, J. Org. Chem., 1992, 57, 6374;
12. b) G.-J. M. Gruter, O. Akkerman, and F. Bickelhaupt, J. Org. Chem., ibid., 1994, 59, 4473.