Glutaric anhydride → HCID 86676095, compound

HRID 1471354Notes

Reaction equation

HRID 1471354 reaction equation
[CH3:1][O:2][C:3]1[C:8]([OH:9])=[CH:7][CH:6]=[C:5](/[CH:10]=[CH:11]/[C:12]([CH2:14][C:15](/[CH:17]=[CH:18]/[C:19]2[CH:27]=[C:24]([O:25][CH3:26])[C:22]([OH:23])=[CH:21][CH:20]=2)=[O:16])=[O:13])[CH:4]=1.CC1C=CN=C(N)C=1C.C(N(CC)CC)C.C1(=O)[O:50][C:48](=[O:49])[CH2:47]CC1>O1CCCC1>[C:48]([OH:50])(=[O:49])[CH3:47].[CH3:26][O:25][C:24]1[C:22]([OH:23])=[CH:21][CH:20]=[C:19](/[CH:18]=[CH:17]/[C:15]([CH2:14][C:12](/[CH:11]=[CH:10]/[C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([OH:9])=[CH:7][CH:6]=2)=[O:13])=[O:16])[CH:27]=1

Participants

6

Reactant 4

HCID 7940Glutaric anhydrideHCID 8471TriethylamineHCID 969516Curcumin2×HCID 110078842-Amino-3,4-dimethylpyridine

Product 1

HCID 86676095HCID 86676095, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

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.

Workup

  1. additionadded in drops
  2. additionaddition funnel
  3. temperatureThe mixture was refluxed
  4. temperatureThe mixture was cooled
  5. concentrationconcentrated
  6. addition50 mL of ethyl acetate was added
  7. temperaturecooled with ice, 20 mL of 0.5 N HCl
  8. additionwas added
  9. customThe organic layer was separated
  10. washwashed with brine
  11. washwash
  12. extractionthe combined solution was extracted with 25 mL of ethyl acetate
  13. dry with materialThe combined ethyl acetate layers were dried over anhydrous sodium sulfate
  14. filtrationfiltered
  15. concentrationconcentrated under vacuum
  16. customto get 1.30 g

Sources & evidence

ORD record
ord-01bcd024622b4073a075ed084beb08e7
Source dataset
uspto-grants-2015_04
Patent number
US09012411B2

Reaction notes

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