A versatile new synthesis of 3-aryl-3H-benzofuran-2-ones

Synlett

Volumn , Issue SPEC. ISS., 1999, Pages 863-864

  Nesvadba, Peter ^a   Bugnon, Lucienne ^a   Dubs, Paul ^a   Evans, Samuel ^a  

^a CIBA GEIGY LTD   (Switzerland)

Author keywords

3 aryl 3H benzofuran 2 ones; 3 hydroxy 3H benzo furan 2 ones; Aromatic hydrocarbon alkylation; Irganox HP; Polymer stabilizers

Indexed keywords

3 BENZOFURANONE DERIVATIVE; 3 BIPHENYL 4 YL 5,7 DI TERT BUTYL 3H BENZOFURAN 2 ONE; 5,7 DI TERT BUTYL 3 (3,5 DIMETHYL 4 HYDROXYPHENYL) 3H BENZOFURAN 2 ONE; GLYOXYLIC ACID; PHENOL DERIVATIVE; UNCLASSIFIED DRUG;

ALKYLATION; ARTICLE; CATALYSIS; CHEMICAL REACTION; DRUG STRUCTURE; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0033008525     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article

References (16)

1. Nesvadba, P.; Evans, S; Kröhnke, Ch.; Zingg J. Ger. Offen. 4432732, 1994; Chem. Abstr. 1995, 123, 55685.
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4. Hewgill, R. F.; Howie, G. B. Aust. J. Chem. 1978, 31, 907.
5. Wasserman, H. H.; Liu, T.-Ch.; Wasserman, E. R. J. Am. Chem. Soc. 1953, 75, 2056.
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10. Kalinin, A.V.; Miah, M. A. J.; Chattopadhyay, S.; Tsukazaki, M.; Wicki, M.; Nguen, T.; Coelho, A.L.; Kerr, M.; Snieckus, V. Synlett 1997, 839.
11. 3): 1.33, 1.39 (2x s, 2x t-Bu), 3.15 (bs, OH), 5.31 (s, 1H), 7.35 (s, 2ArH). Similarly: (1a): resin, purified by chromatography on silica gel, δH: 1.31 (s, t-Bu), 2.29 (s, Me), 3.53 (bs, OH), 5.33 (s, 1H), 7.21, 7.33 (2x s, 2x 1ArH); (1b); m.p. 158-160 °C, δH: 1.37 (s, t-Bu), 2.35 (s, Me), 3.26 (bs, OH), 5.30 (s, 1H), 7.11, 7.13 (2x s, 2x 1ArH); (1d): resin, δH: 1.1-1.9 (m, 20H), 2.3-2.6 (m, 1H), 2.7-2.9 (m, 1H), 3.73 (bs, OH), 5.29 (s, 1H), 7.08, 7.15 (2x s, 2x 1ArH).
12. 3): 1.29, 1.46 (2x s, 2x t-Bu), 2.22 (s, 2x Me), 4.60 (bs, OH), 4.69 (s, 1H), 6.82 (s, 1ArH), 7.03 (d, J=2.9Hz, 1ArH), 7.26 (s, 1ArH), 7.31 (d, J=2.9Hz, 1ArH).
13. 3): 1.25, 1.44 (2x s, 2x t-Bu), 1.70, 2.14, 2.26, 2.32, 2.46 (5x s, 5x Me), 5.36 (s, 1H), 6.86, 7.25 (2x s, 2x 1ArH).
14. 3): 1.29, 1.44 (2x s, 2x t-Bu), 4.84 (s, 1H), 7.06-7.46 (m, 7ArH).
15. 4 activated montmorillonite supplied by LAPORTE, Moorfield Road, Widnes, Cheshire, UK.
16. 3): 1.27, 1.45 (2x s, 2x t-Bu), 2.26 (bs, 2x Me), 5.00 (bs, 1H), 6.75-7.30 (m, 5ArH). Similarly: 5,7-di-tert-butyl-3-(3,4-dimethylphenyl)-3H-benzofuran-2-one (entry 3): m.p. 130-132 °C, δH: 1.29, 1.44 (2x s, 2x t-Bu), 2.25 (s, 2x Mc), 4.76 (s, 1H), 6.91-7.32 (m, 5ArH); 5,7-di-tert-butyl-3-(4-methoxyphenyl)-3H-benzofuran-2-one (entry 5): m.p. 102-104 °C, δH: 1.29, 1.43 (2x s, 2x t-Bu), 3.80 (s, McO), 4.78 (s, 1H), 6.87-7.33 (m, 6ArH); 3-biphenyl-4-yl-5,7-di-tert-butyl-3H-ben-zofuran-2-one (entry 7): m.p. 168-170°C, δH: 1.31, 1.45 (2x s, 2x t-Bu), 4.89 (s, 1H), 7.10-7.61 (m, 11ArH); 5,7-di-tert-butyl-3-thiophen-2-yl-3H-benzofuran-2-one (entry 8): m.p. 86-93 °C, δH: 1.32, 1.42 (2x s, 2x t-Bu), 5.09 (s, 1H), 6.94-7.38 (m, 5ArH); 5,7-di-tert-butyl-3-dibenzofuran-2-yl-3H-benzofuran-2-one (entry 9): m.p. 150-154 °C, δH: 1.30, 1.52 (2x s, 2x t-Bu), 5.00 (s, 1H), 7.09-7.94 (m, 9ArH).