Tetrabutylammonium Fluoride → 10-Fluoro-4-thia-decanoic acid

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Reaction Steps

Compound 5 (0.5 g, 1,8 mmol) was caused to react with TBAF (3 mmol) according to the procedure for compound 2. The resultant fluoroester was hydrolyzed in KOH/ethanol as previously described, and isolated as an oil by HPLC (Table 1) to yield 0.14 g (37% yield) product 6. 1H-NMR δ1.3 (m, 8H, 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)H2JHF=47.5 Hz, JHH=6.2 Hz).

Provenance & Evidence