Ammonia → 12-fluoro-(E)-3-dodecen-1-ol

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Reaction Steps

A solution of 12-fluoro-3-dodecyn-1-yl tetrahydropyranyl ether (1.42 g, 5 mmol) in dry tetrahydrofuran (50 ml.) is added slowly to a solution of sodium (920 mg., 40 mmol) in liquid ammonia (300 ml), the colour changing from blue through violet and red to a dull orange. More sodium (1.84 g, 80 mmol) is then added, the mixture becoming green then blue. The volume is increased to 500 ml. with liquid ammonia and the mixture stirred for two hours, after which dry ammonium chloride is added slowly until the color changed to pale yellow. After evaporation of the ammonia the residue is treated with dilute hydrochloric acid (6N., 50 ml.) and thoroughly extracted with ether. The neutral fraction is chromatographed on alumina (grade III, 30 g.). Elution with light petroleum yields 12-fluoro-(E)-3-dodecen-1-ol as a colourless oil, IR (film) 966 cm-1 (Trans C=C).

Provenance & Evidence