Pyridine → 9-Octadecene, 1-chloro-

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Reaction Steps

This compound was prepared according to the method of Levantis and Silvius (1990). Oleyl chloride was prepared by slowly adding 3 ml (35 mmol) of oxalyl chloride to 1.0 g (3.5 mmol) oleic acid dissolved in 10 ml benzene without stirring at room temperature for 1 hour. After removal of solvent and excess oxalyl chloride under vacuum, the acid chloride was dissolved in 5 ml diethyl ether, and a further 5 ml of ether containing 0.20 g (1.7 mmol) of 3,N,-dimethylamino-1,2-propanediol and 0.15 g pyridine was added. The resulting mixture was stirred at room temperature for 30 minutes before quenching with 1 ml methanol. Solvents were removed under vacuum. The crude product was dissolved in 50 ml hexane and washed with 2×25 ml 0.1M sodium chloride. Drying over anhydrous sodium sulfate, and removal of hexane under vacuum gave a slightly yellow oil. Column chromatography on silica gel (70-230 mesh), wherein elution was with ethyl acetate, gave 0.92 g (84%) of pure product (TLC, Rf=0.5). 200 MHz 1H-NMR (CDCl3), δ ppm from TNS (J-coupling, integration): 5.3 (dd, 4H), 5.1 (m, 1H), 4.0 (dd, 1 h), 2.4 (dd, 2H), 2.2 (s, 6H), 2.0-0.8 (m, 62H). This procedure was also used to prepare the deuterated analog rac-1-N,N-dimethylamino-2,3-bis(9,10-dideuteriooleoyl)propane (AL-1-d4) and ±-1,2-didecanoyl-1-N,N,-dimethyl-aminopropane (AL-6).

Provenance & Evidence