Diethyl Ether → Dimethylcurcumin

HRID 218108Notes

Reaction equation

HRID 218108 reaction equation
[CH3:1][O:2][C:3]1C(O)=C[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.[N+](=[CH2:30])=[N-].C[CH2:32][O:33][CH2:34][CH3:35]>CO>[CH3:32][O:33][C:34]1[CH:35]=[CH:6][C:5](/[CH:10]=[CH:11]/[C:12](/[OH:13])=[CH:14]/[C:15](/[CH:17]=[CH:18]/[C:19]2[CH:20]=[CH:21][C:22]([O:23][CH3:30])=[C:24]([O:25][CH3:26])[CH:27]=2)=[O:16])=[CH:4][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 9550DiazomethaneHCID 969516Curcumin

Product 1

HCID 6477182DimethylcurcuminYield 19.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Curcumin (1) in Et2O and MeOH was treated with excess of diazomethane in ether for 24 h. The solvents were removed in vacuo and the residue was purified by silica gel column chromatography and PLC to yield yellow needles of 4 (yield 19.8%); mp 129-130° C. (MeOH) (Roughley et al., J. Chem. Soc. Perkin I, 2379-2388 (1973)) (128-130° C.); 1H NMR (300 MHz, CDCl3): δ 3.93 (12H, s, OCH3×4), 5.82 (1H, s, 1-H), 6.48 (2H, d, 16 Hz), 6.88 (2H, d, J=8 Hz), 7.08 (2H, bs), 7.15 (2H, bd), 7.61 (2H, J=16 Hz); 13CNMR (300 MHz, CDCl3): δ 55.9, 56.0, 101.3, 109.8, 111.1, 122.0, 122.6, 128.1, 140.4, 149.2, 151.0, 183.2.

Workup

  1. customThe solvents were removed in vacuo
  2. customthe residue was purified by silica gel column chromatography and PLC

Sources & evidence

ORD record
ord-a7cd8b8565b541729adcab2bfe91c993
Source dataset
uspto-grants-2012_06
Patent number
US08198323B2

Reaction notes

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