Vanillin → HCID 86653389, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of boric oxide (183 mg, 2.65 mmol) in DMF (1 mL), was added acetyl acetone (0.236 mL, 2.30 mmol) followed by tributyl borate (1.25 mL, 4.62 mmol) at rt and stirred at 65° C. for 15 min. To the above borate complex, a mixture of 3-methoxy-4-docosahexaenoyloxybenzaldehyde (1 g, 2.30 mmol) and vanillin (350 mg, 2.30 mmol) was added and stirred for 5 min at the same temperature. A mixture of n-butyl amine (0.045 mL) and acetic acid (0.13 mL) in DMF (1 mL) was added to the reaction mixture and stirred at 90-95° C. for 4 h. After cooling to 15° C., acetic acid (20%, 20 mL) was added with stirring and again the reaction mixture was stirred at 70° C. for another 1 h. Then it was cooled to rt, extracted with chloroform (3×100 mL) and the combined chloroform layer was washed with water, brine and dried over sodium sulfate. The solution was filtered and the residue was chromatographed over silica gel column using hexane-ethyl acetate (85:15) as eluents to give 1-(4-docosahexaenoyloxy-3-methoxyphenyl)-7-(4-hydroxy-3-methoxyphenyl)-1,6-heptadiene-3,5-dione (400 mg, 25%). LCMS (ESI, negative ion mode): m/z (M-H)−.

Provenance & Evidence