Reaktion #90866

Reaktionsgleichung

Mono-Propargyl Curcumin

2-(2-(2-azidoethoxy)ethoxy)ethanol

sodium ascorbate

→

Mono-2-(2-(2-(4-(methylene)-1H-1,2,3-triazol-1-yl)ethoxy)ethoxy)ethanol-curcumin

Ausbeute 26.0%

Lösungsmittel

tBuOH

CHCl3

H2O

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigewas removed under vacuum
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in CHCl3
3. 3
   Waschenwashed with H2O
4. 4
   Sonstigethe organic phase was separated
5. 5
   Trocknendried over Na2SO4
6. 6
   Sonstigeevaporated
7. 7
   SonstigePurification
8. 8
   Wascheneluting with CH2Cl2—CH2Cl2

Vorschrift

To a stirred solution of Mono-Propargyl Curcumin 5 (63 mg, 0.16 mmol) and 2-(2-(2-azidoethoxy)ethoxy)ethanol (46 mg, 0.26 mmol) in tBuOH (1.1 mL) and CHCl3 (0.3 mL) was added a prepared solution of Cu(OAc)2 (8 mg, 0.03 mmol) and sodium ascorbate (13 mg, 0.07 mmol) in H2O (1.3 mL). After vigorous stirring overnight the solvent was removed under vacuum. The mixture was dissolved in CHCl3, washed with H2O and the organic phase was separated, dried over Na2SO4 and evaporated. Purification was performed by column chromatography, eluting with CH2Cl2—CH2Cl2: MeOH 98:2. Yield 26%. NMR 1H (CDCl3), δ (ppm): 3.55-3.60 (m, 8H); 3.72-3.72 (t, 3H); 3.87-3.94 (m, 8H); 4.54-4.55 (t, 2H); 5.80 (s, 1H); 6.07 (s, 1H); 6.46-6.50 (dd, 2H); 6.92-6.94 (d, 1H); 7.05-7.12 (m, 5H); 7.56-7.60 (q, 2H); 7.92 (s, 1H).). MS (ESI) calcd. for C30H35N3O9: 581.61. found: 582.3 [M+H]+, 604.3 [M++Na], 620.3 [M++K].

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