Sodium Iodide → 22-iododocosanoic Acid

Participants

Reaction Steps

21-Docosenoic acid (55mg. 0.16 mmol) was hydroborated with dicyclohexylborane (0.32 mmol) at 0° C. The organoborane was iodinated with a mixture of sodium aceate (0.32 mmol), sodium iodide (0.16 mmol), and chloramine-T (0.32 mmol). The product was isolated by a column chromotography on silica gel (10% ethyl acetate:hexane):yield 68 mg (91%); mp 71°-2° C.; m/e 466.5 (calcd 466.5); NMR (CDCl3), 1.2 δ (s, 36H, alkane), 2.1 (m, 4H, --CH2 --CO2H and --CH2CH2I), 3.0 (t, 2H, --CH2I, 11.9 (s, 1H, --CO2H).

Provenance & Evidence