Water → Mono-Propargyl Curcumin

HRID 452021Notes

Reaction equation

HRID 452021 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([O-])([O-])=O.[K+].[K+].[CH2:34](Br)[C:35]#[CH:36].O>CN(C=O)C>[CH2:36]([CH:14]([C:12](/[CH:11]=[CH:10]/[C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:8]([OH:9])=[CH:7][CH:6]=1)=[O:13])[C:15](=[O:16])/[CH:17]=[CH:18]/[C:19]1[CH:27]=[C:24]([C:22]([OH:23])=[CH:21][CH:20]=1)[O:25][CH3:26])[C:35]#[CH:34]

Participants

6

Reactant 4

HCID 962WaterHCID 7842Propargyl bromideHCID 11430Potassium CarbonateHCID 969516Curcumin

Product 1

HCID 88539422Mono-Propargyl CurcuminYield 47%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Curcumin (5 g, 13.57 mmol) and K2CO3 (1.88 g, 13.62 mmol) were dissolved in 60 mL DMF, and 1.62 g (13.61 mmol) of propargyl bromide was added. The mixture was stirred at room temperature under Ar for 49 h. H2O was added to the mixture and solvent was removed under vacuum. The product was purified on column chromatography, eluting with CH2Cl2: hexane 50:50- CH2Cl2. Yield 47%. NMR NMR 1H (CDCl3), δ (ppm): 2.54 (s, 1H); 3.94 (d, 6H); 4.81 (d, 2H); 5.82 (s, 1H); 5.93 (s, 1H); 6.47-6.52 (t, 2H); 6.93-7.15 (m, 6H); 7.59-7.61 (dd, 2H). MS (ESI) calcd. for C24H22O6: 406.43. Found: 407.2 [M+H]+, 445.2 [M++K].

Workup

  1. customwas removed under vacuum
  2. customThe product was purified on column chromatography
  3. washeluting with CH2Cl2: hexane 50:50- CH2Cl2

Sources & evidence

ORD record
ord-1b6f33a5b5dd4a719829356e00da0c65
Source dataset
uspto-grants-2013_07
Patent number
US08487139B2

Reaction notes

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