Pyridine → HCID 86678083, compound

Participants

Reaction Steps

Linoleoyl chloride (25.0 g, 83.6 mmol) was added, dropwise, to a cooled (0° C.) solution of Meldrum's acid (1) (13.3 g, 92.0 mol) and pyridine (14.8 mL, 184 mmol) in CH2Cl2 (180 mL) and the solution was allowed to warm (rt, 16 h). The reaction mixture was washed with an equal volume of HCl (5%, aq., 2×), dried (Na2SO4), filtered and concentrated. The residue was dissolved in dry methanol (200 mL) and heated at reflux (6 h). The solution was cooled (rt), concentrated and the crude oil was purified by flash chromatography (4% EtOAc-hexanes) to yield (11Z,14Z)-methyl 3-oxoicosa-11,14-dienoate (2) (24.5 g, 87%) as a pale yellow oil. Rf 0.38 (10% EtOAc-hexanes). FW 336.51, C21H36O3.

Provenance & Evidence