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Volumn , Issue 4, 2008, Pages 605-607

A simple and efficient method for transesterification of β-keto esters catalyzed by cesium fluoride

Author keywords

keto esters; Alcohols; Catalysis; Cesium fluoride; Transesterifications

Indexed keywords

ALCOHOL DERIVATIVE; CESIUM FLUORIDE; ESTER DERIVATIVE; FLUORIDE; UNCLASSIFIED DRUG;

EID: 40949091542     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1032071     Document Type: Article
Times cited : (12)

References (39)
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    • To the best of our knowledge, there is only one successful report 4 on the use of this type compound in the transesterification process
    • 4 on the use of this type compound in the transesterification process.
  • 30
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    • CsF was the best catalyst among the cesium salts examined under the identical conditions: CsCl (1%), CsBr (2%), CsI (2%).
    • CsF was the best catalyst among the cesium salts examined under the identical conditions: CsCl (1%), CsBr (2%), CsI (2%).
  • 31
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    • Transesterification of β-keto esters with allylic alcohols is rather difficult as it is offset by facile decarboxylative rearrangement: (a) Carrol, M. F. J. Chem. Soc. 1940, 704
    • Transesterification of β-keto esters with allylic alcohols is rather difficult as it is offset by facile decarboxylative rearrangement: (a) Carrol, M. F. J. Chem. Soc. 1940, 704.
  • 33
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    • Conventional acid- and base-catalyzed transesterification of β-keto esters with propargylic alcohols provided in most cases low yields of the products: Mottet, C, Hamelin, O, Garavel, G, Depres, J.-P, Greene, A. E. J. Org. Chem. 1999, 64, 1380; and references cited therein
    • Conventional acid- and base-catalyzed transesterification of β-keto esters with propargylic alcohols provided in most cases low yields of the products: Mottet, C.; Hamelin, O.; Garavel, G.; Depres, J.-P.; Greene, A. E. J. Org. Chem. 1999, 64, 1380; and references cited therein.
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    • Cesium fluoride promoted desilylation of tert- butyldimethylsilyl ethers was reported: Cirillo, P. F.; Panek, J. S. J. Org. Chem. 1990, 55, 6071.
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    • Transesterification of normal esters proceeded under similar reaction conditions. The details of this result will be communicated later
    • Transesterification of normal esters proceeded under similar reaction conditions. The details of this result will be communicated later.
  • 36
    • 40949130086 scopus 로고    scopus 로고
    • 23 CsF remained intact and was reused for the subsequent reaction.
    • 23 CsF remained intact and was reused for the subsequent reaction.
  • 37
    • 40949107397 scopus 로고    scopus 로고
    • Purchased from Mitsuwa Chemicals Co, Ltd
    • Purchased from Mitsuwa Chemicals Co., Ltd.
  • 38
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    • The equilibrium was shifted due to the loss of the relatively volatile methyl, ethyl or isopropyl alcohol from the reaction mixture
    • The equilibrium was shifted due to the loss of the relatively volatile methyl, ethyl or isopropyl alcohol from the reaction mixture.
  • 39
    • 40949117716 scopus 로고    scopus 로고
    • Selected spectroscopic data: Octyl 2,2-Dimethyl-3-oxobutyrate: 1H NMR (CDCl3, δ, 0.88 (t, J, 7.5 Hz, 3 H, 1.22-1.66 (m, 12 H, 1.36 (s, 6 H, 2.16 (s, 3 H, 4.12 (t, J, 7.0 Hz, 2 H, 13C NMR (CDCl3, δ, 13.9, 21.7, 22.5, 25.5, 25.7, 28.3, 29.0, 31.6, 55.6, 65.3, 173.5, 205.6. 2-Heptynyl 3-Oxohexanoate: 1H NMR (CDCl3, δ, 0.91 (t, J, 7.5 Hz, 3 H, 0.93 (t, J, 7.5 Hz, 3 H, 1.36-1.44 (m, 2 H, 1.46-1.53 (m, 2 H, 1.59-1.67 (m, 2 H, 2.22 (tt, J, 2.5, 7.5 Hz, 2 H, 2.53 (t, J, 7.5 Hz, 2 H, 3.47 (s, 2 H, 4.72 (t, J, 2.5 Hz, 2 H, 13C NMR (CDCl3, δ, 13.4, 16.8, 18.3, 21.8, 30.3, 44.7, 48.9, 53.5, 73.3, 88.0, 166.5, 202.1. 8-Oxiranyloctyl 3-Oxohexanoate: 1H NMR (CDCl3, δ, 0.93 (t, J, 7.5 Hz, 3 H, 1.25-1.69 (m, 16 H, 2.47 dd, J, 3.5, 5.0 Hz, 1 H, 2
    • 3): δ = 13.4, 16.8, 25.0, 26.3, 28.2, 32.2, 44.7, 49.1, 65.0, 167.1, 202.6.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.