Dicyclohexylcarbodiimide → 22-Linoleoyloxydocosanoic Acid, Tert.-Butyl Ester

Participants

Reaction Steps

A solution containing tert.-butyl 22-hydroxydocosanoate (34) (2.17 g, 5.26 mmol) and linoleic acid (1.45 g, 5.26 mmol) in dry ethanol free chloroform (50 ml) at room temperature under nitrogen was treated with dimethylaminopyridine (0.064 g, 0.524 mmol) and dicyclohexylcarbodiimide (1.19 g, 5.78 mmol), and the resulting solution was stirred for three hours at room temperature, after which time tlc indicated that the reaction is complete. The mixture was filtered and the filtrate washed with 5% acetic acid, then water, then dried (MgSO4), filtered and evaporated. The residue was purified by chromatography on silica (30 g). Elution with petrol followed by 5% ether in petrol gave the title compound (35) as a white wax (2.18 g, 79%).

Provenance & Evidence