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Volumn 61, Issue 18, 1996, Pages 6456-6457

Molar scale synthesis of enantiopure stilbene oxide

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EID: 0000776037     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960718q     Document Type: Article
Times cited : (45)

References (83)
  • 75
    • 3643059631 scopus 로고
    • Shapiro, A. L.; Leven, S. Z.; Chekhovskaya, V. P. Zh. Org. Kh. 1969, 5, 207; J. Org. Chem. USSR, 1969, 5, 200.
    • (1969) J. Org. Chem. USSR , vol.5 , pp. 200
  • 76
    • 85033821086 scopus 로고    scopus 로고
    • US Patent 4 265 821, 1981; UK Patent GB 2 092 126 A, 1981; US Patent 4 371 704, 1983
    • McEntire, E. E.; Gipson, R. M. US Patent 4 265 821, 1981; UK Patent GB 2 092 126 A, 1981; US Patent 4 371 704, 1983.
    • McEntire, E.E.1    Gipson, R.M.2
  • 77
    • 85033813776 scopus 로고    scopus 로고
    • note
    • (a) The following control experiment was performed: a sample of stilbene oxide (3) (99% ee) was subjected to the reaction conditions overnight, whereupon ca. 90% of the epoxide had rearranged to deoxybenzoin, the major byproduct in the actual process. The enantiopurity of recovered 3 was reduced to 75% ee, and traces of the mesoepoxide and diphenylacetaldehyde were also detected,
  • 78
    • 85033818833 scopus 로고    scopus 로고
    • note
    • 3. The reaction should be stopped when the epoxide to carbonate ratio is about 20:1.
  • 81
    • 85033805806 scopus 로고    scopus 로고
    • note
    • This silica gel filtration is very important. It removes the LiCl which otherwise causes decomposition of the epoxide during recrystallization from boiling MeOH.
  • 82
    • 85033817271 scopus 로고    scopus 로고
    • note
    • The recrystallization is performed in an Erlenmeyer flask with a magnetic stir bar. The epoxide is added followed by the appropriate volume of MeOH and the mixture is heated to boiling while being stirred. The hot solution is then allowed to cool gradually to room temperature and the crystalline product is collected by filtration.
  • 83
    • 37049154148 scopus 로고
    • Epoxide 3 appears to be a racemic compound for which the enantiopure substance and the racemate have coincidentally the same melting point. Read, J.; Campbell, I. G. M. J. Chem. Soc. 1930, 2377.
    • (1930) J. Chem. Soc. , pp. 2377
    • Read, J.1    Campbell, I.G.M.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.