Diethyl Ether → HCID 131732740, compound

HRID 1471356Notes

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.C(N(CC)CC)C.[C:35]1(=[O:42])[O:41][C:39](=[O:40])[CH2:38][CH2:37][CH2:36]1.CC[O:45]CC>CN(C1C=CN=CC=1)C.C1COCC1>[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.[C:35]([O-:41])(=[O:42])[CH2:36][CH2:37][CH2:38][C:39]([O-:45])=[O:40]

Participants

Conditions

Temperature: 80 °C

Procedure

In a 500 mL round bottom flask curcumin (3.00 g), DMAP (168 mg) and triethyl amine (4 ml) were taken in 150 mL of THF. Glutaric anhydride (2.35 ml) in 15 mL of THF was added drop-wise under anhydrous conditions. The mixture was refluxed for 20 hours at 80° C. The solution was evaporated in a rotovop. The thick residue was taken in 150 mL of ethyl acetate, washed with 50 mL of 0.5 N HCl. The HCl wash was extracted with 50 mL of ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous sodium sulfate and was concentrated under vacuum to get 4.80 g. This was co-evaporated with ether several times to get a solid, 2.5 g. NMR was consistent with the structure.

Workup

customThe solution was evaporated in a rotovop
washwashed with 50 mL of 0.5 N HCl
washThe HCl wash
extractionwas extracted with 50 mL of ethyl acetate
dry with materialThe combined ethyl acetate extracts were dried over anhydrous sodium sulfate
concentrationwas concentrated under vacuum
customto get 4.80 g

Sources & evidence

ORD record: ord-120a838ada2e49239a665c1c539c93f5
Source dataset: uspto-grants-2015_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09012411B2

Reaction notes

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