Reaktion #1973923

Reaktionsgleichung

p-aminophenylethanol

triethyl amine

N-hydroxysuccinimide-(4-pentynoate)

→

N-(4-(2-(Hydroxy)Ethyl)Phenyl)Pent-4-Ynamide

Lösungsmittel

dichloromethane

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe crude reaction product
2. 2
   Einengenwas concentrated
3. 3
   workup.DISSOLUTIONdissolved in 10 mL of ethyl acetate
4. 4
   Waschenwashed with 5 mL of water
5. 5
   TrocknenThe organic phase was dried with MgSO4
6. 6
   Filtrationfiltered
7. 7
   Sonstigethe solvent was evaporated
8. 8
   SonstigeThe product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E)

Vorschrift

N-hydroxysuccinimide-(4-pentynoate) (Ref: Malkoch, M.; Schleicher, K.; Drockenmuller, E.; Hawker, C. J.; Russell, T. P.; Wu, P.; Fokin, V. V., Structurally Diverse Dendritic Libraries: A Highly Efficient Functionalization Approach Using Click Chemistry. Macromolecules 2005, 38, (9), 3663-3678.) (200 mg, 1.0 mmol) and p-aminophenylethanol (125 mg, 0.9 mmol) were dissolved in 2 mL of dichloromethane together with triethyl amine (140 μL, 1.0 mmol), and 5 drops of dimethyl formamide. The reaction mixture was stirred at room temperature for 2 hours. The crude reaction product was concentrated, dissolved in 10 mL of ethyl acetate and washed with 5 mL of water followed by, 5 mL of 0.5 M HCl (aq.), 5 mL of 10 NaHCO3 (aq.) and finally 5 mL of water. The organic phase was dried with MgSO4, filtered, and the solvent was evaporated. The product was further purified by column chromatography on silica gel eluting with a gradient of toluene (T) and ethyl acetate (E) from 4:1 to 1:2 (T:E). The product N-(4-(2-(hydroxy)ethyl)phenyl)pent-4-ynamide was characterized by NMR and MALDI-TOF.

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