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Volumn 2005, Issue 3, 2005, Pages 211-220

Synthesis of fluorine containing 3-cyano/ethoxycarbonyl-2-ethylbenzo[b] furans via microwave assisted tandem intramolecular Wittig and Claisen rearrangement reactions

Author keywords

2 ethylbenzo b furan 3 carbonitrile; 2 (Aryloxy)propanoyl (cyano ethoxycarbonyl) methylene triphenylphosphoranes; Claisen rearrangement; Ethyl 2 ethyl benzo b furan 3 carboxylate; Intramolecular Wittig reaction; ortho allenylphenol

Indexed keywords

3 CYANO 2 ETHYL 5 FLUOROBENZO[B]FURAN; 3 CYANO 5, 7 DIFLUORO 2 ETHYLBENZO[B]FURAN; 3 ETHOXYCARBONYL 2 ETHYL 5 FLUOROBENZO[B]FURAN; 6 CHLORO 3 CYANO 2 ETHYL 5 FLUOROBENZO[B]FURAN; 7 CHLORO 2 ETHYL 5 FLUOROBENZO[B]FURAN; 7 CHLORO 3 CYANO 2 ETHYL 5 FLUOROBENZO[B]FURAN; 7 CHLORO ETHOXYCARBONYL 2 ETHYL 5 FLUOROBENZO[B]FURAN; BENZOFURAN DERIVATIVE; FLUORINE DERIVATIVE; PHOSPHINE DERIVATIVE; PHOSPHORANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 15444381277     PISSN: 14246376     EISSN: None     Source Type: Journal    
DOI: None     Document Type: Article
Times cited : (10)

References (26)
  • 1
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    • Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V. Eds.; Pergamon, New York
    • Keay, B.A.; Dibble, P.W. Comprehensive Heterocyclic Chemistry II, Katritzky, A.R.; Rees, C.W.; Scriven, E.F.V. Eds.; Pergamon, New York, 1996, Vol. 2, p 395.
    • (1996) Comprehensive Heterocyclic Chemistry II , vol.2 , pp. 395
    • Keay, B.A.1    Dibble, P.W.2
  • 3
    • 0030939744 scopus 로고    scopus 로고
    • and references cited therein
    • Ward, R.S. Nat.Prod.Rep. 1997, 14, 43 and references cited therein.
    • (1997) Nat.Prod.Rep. , vol.14 , pp. 43
    • Ward, R.S.1
  • 21
    • 15444370861 scopus 로고
    • Fodor, T.; Rozsa, L.; Vago, P. Hung.Teljes HU 1982, 24005; Chem. Abstr. 1983, 99, 70551.
    • (1983) Chem. Abstr. , vol.99 , pp. 70551
  • 25
    • 15444363748 scopus 로고    scopus 로고
    • note
    • Fluorophenol (41 mmole) and 50% aqueous 2-chloro-propanoic acid (41 mmol) were refluxed with 33% aqueous sodium hydroxide (82 mmol, 10 ml) solution for 3h. The reaction mixture is cooled and neutralized with 5% dilute HCl (15 ml). The precipitated 2-fluorophenoxy-propanoic acid was filtered, washed with water (2x20 ml) and dried (yield: 88-94%). The fluorophenoxypropanoic acid was refluxed with 2 equivalents of thionyl chloride in hexane (10 ml) for 1-2 h. After removing hexane and excess thionyl chloride, pure fluoroaryloxypropanoyl chloride was obtained by distillation under reduced pressure (yield: 81-85%).


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