Propiolic Acid → HCID 87566223, compound

Participants

Reaction Conditions

Reaction Steps

1H,1H,2H,2H-perfluoro-1-octanol (10.1 g, 27.7 mmol) and propiolic acid (1.70 mL, 27.7 mmol) were dissolved in methylene chloride (15 mL), and the resulting solution cooled to 0° C. under nitrogen. To this was added a solution of dicyclohexylcarbodiimide (5.72 g, 27.7 mmol) and para-dimethylaminopyridine (0.034 g, 0.28 mmol) in methylene chloride (15 mL) over a 1 hour period, with stirring. The mixture was then allowed to warm to room temperature and a tan solid (dicyclohexylurea) precipitated. The reaction mixture was stirred overnight and then filtered to remove the dicyclohexylurea, and the filtrate was concentrated under vacuum to afford the crude product as a red oil. The crude product was chromatographed on a 15 cm×5 ccm silica gel column using 15% ethyl acetate in hexane to afford 8.31 g of (3,3,4,4,5,5,6,6,7,7,8,8,8-tridecafluorooctyl) propiolate as a yellow oil (72% yield).

Provenance & Evidence