Ethanol → 16-Fluoro-4-thia-hexadecanoic acid

Participants

Reaction Steps

Fluorination of 1 (0.2 g, 0.5 mmol) was performed by addition of tetrabutylammonium fluoride (TBAF) (4 mmol as 1M THF solution). The mixture was allowed to react at room temperature for 20 h. The resulting fluoro-ester was hydrolyzed by addition of 1 ml 1 N KOH and 1 ml ethanol for 2 h at room temperature. The product 2 (0.05 g, 34% yield) was isolated by column chromatography (hexane/ether/acetic acid 3:1:0.1) and recrystallized in hexane, TLC (hexane/ether/acetic acid 3:1:0.1) Rf=0.25. Melting point=59° C., 1H-NMR δ1.4 (m, 20H, CH2), 2.55 (t, 2H, C(2)H2), 2.65 (t, 2H, C(5)H2), 2.80 (t, 2H, C(3)H2), 4.44 (dt, 2H, C(16)H2JHH=6.2 Hz).

Provenance & Evidence