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6,8,11,14-Eicosatetraenoic acid, 5-hydroxy-, methyl ester, (6E,8Z,11Z,14Z)- synthesis

9synthesis methods
81517-87-5 Synthesis
5-hydroxyeicosatetraenoic acid lactone

81517-87-5
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6,8,11,14-Eicosatetraenoic acid, 5-hydroxy-, methyl ester, (6E,8Z,11Z,14Z)-

70968-99-9
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Yield:70968-99-9 87%

Reaction Conditions:

with triethylamine in methanol at 20; for 6 h;

Steps:

4.2.8. Preparation of hydroxy methyl esters 6a-6c(method C)

General procedure: These compounds were prepared according to literature procedures.43,44 A solution of lactone (1.00 equiv.) in MeOH (52.0 mM) wasadded Et3N (3.00 equiv.). The reaction mixture was stirred for six hoursat ambient temperature and the solvent was removed in vacuo. Theproduct was purified by column chromatography on silica (heptane/EtOAc 85:15) to afford the corresponding hydroxy methyl ester.

References:

Stepniewski, Tomasz Maciej;Torrens-Fontanals, Mariona;Rodríguez-Espigares, Ismael;Giorgino, Toni;Primdahl, Karoline G.;Vik, Anders;Stenstr?m, Yngve;Selent, Jana;Hansen, Trond Vidar [Bioorganic and Medicinal Chemistry,2018,vol. 26,# 12,p. 3580 - 3587]