Glutaric anhydride → HCID 86676095, compound

Participants

Reaction Steps

Curcumin (1.00 g) was dissolved in tetrahydrofuran (50 ml) in a 250 mL round bottom flask under a flow of nitrogen gas. Dimethyl amino pyridine (56 mg) and triethyl amine (1.33 ml) were added. The color changed from yellow to light red. Glutaric anhydride (50 ml) was dissolved in 5 mL of tetrahydrofuran and added in drops using a pressure equalizing addition funnel. The mixture was refluxed and stirred over night. The mixture was cooled and concentrated. 50 mL of ethyl acetate was added, cooled with ice, 20 mL of 0.5 N HCl was added. The organic layer was separated and washed with brine. The brine was combined with the HCl wash, and the combined solution was extracted with 25 mL of ethyl acetate. The combined ethyl acetate layers were dried over anhydrous sodium sulfate, filtered, concentrated under vacuum to get 1.30 g. TLC indicated no curcumin, NMR consistent with structure.

Provenance & Evidence