Reaction #90866

Reaction equation

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

Yield 26.0%

Solvents

tBuOH

CHCl3

H2O

Conditions

Workup

1. 1
   Otherwas removed under vacuum
2. 2
   workup.DISSOLUTIONThe mixture was dissolved in CHCl3
3. 3
   Washwashed with H2O
4. 4
   Otherthe organic phase was separated
5. 5
   Dryingdried over Na2SO4
6. 6
   Otherevaporated
7. 7
   OtherPurification
8. 8
   Washeluting with CH2Cl2—CH2Cl2

Procedure

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].

Source