Novel tocopherol compounds XI. Synthesis, bromination and oxidation reactions of 3-(5-tocopheryl)propionic acid

Synlett

Volumn , Issue 3, 1999, Pages 291-294

  Rosenau, Thomas ^a   Habicher, Wolf D ^b   Potthast, Antje ^a   Kosma, Paul ^a  

^a UNIVERSITY OF NATURAL RESOURCES AND LIFE SCIENCES   (Austria)

^b DRESDEN UNIVERSITY OF TECHNOLOGY   (Germany)

Author keywords

5a substituted tocopherols; Hetero Diels Alder reaction; Ketene acetal; Ortho quinone methide; Tocopherol

Indexed keywords

2 QUINONE METHIDE; 3 (5 TOCOPHERYL)PROPIONIC ACID; ALPHA TOCOPHEROL; O METHYL C,O BIS(TRIMETHYLSILYL)KETENE ACETAL; REAGENT; TOCOPHEROL DERIVATIVE; UNCLASSIFIED DRUG;

ARTICLE; BROMINATION; DRUG OXIDATION; DRUG SYNTHESIS; REACTION ANALYSIS;

EID: 0033057487     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1999-2594     Document Type: Article

References (29)

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17. 3), 63.8 and 72.5 (s, 1H, HC=C), 161.4 and 164.5 (HC=C).
18. 13C spectrum shows a ortholactone signal at 108.4 ppm, but no indication of an ester carbon atom.
19. 4. The oily residue remaining after evaporation of the solvent was used for further reactions without purification. An analytical sample of 12 was prepared by chromatography on neutral aluminum oxide.
20. 4 (488.75): C, 76.18; H, 10.72. Found: C, 76.24; H, 10.88. For the reason of clarity, the resonances of the isoprenoid side chain are not listed here and in the following. The convention of numbering carbon atoms in vitamin E derivatives is explained in (14b).
21. 4Br (567.64): C, 65.59; H, 9.06; Br, 14.08. Found: C, 65.45; H, 8.99; Br, 14.12.
22. 8 (973.48): C, 76.50; H, 13.15. Found: C, 76.62; H, 13.23.
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