Reaktion #5347

Reaktionsgleichung

tetronic acid

triethylamine

HCl

1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride

6-(4-heptylphenoxy)heptanoic acid

→

3-[6-(4-heptylphenoxy)-1-oxohexyl]-4-hydroxy-2(5H)-furanone

Ausbeute 50.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Extraktionextracted with three 200 mL portions of ether
2. 2
   TrocknenThe combined organic layers are dried over MgSO4
3. 3
   Einengenconcentrated in vacuo

Vorschrift

To a stirring solution of 1.1 g (10.98 mmol) of tetronic acid in 25 mL of dimethylformamide is added 1.53 mL (10.98 mmol) of triethylamine and 400 mg of 4-dimethylaminopyridine at 0° C. Next, 2.28 g (11.98 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.38 g (10.98 mmol) of 6-(4-heptylphenoxy)heptanoic acid are added and the reaction mixture is stirred for 3 days at room temperature. The reaction mixture is acidified with 1.0N HCl and extracted with three 200 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo. Trituration of the crude product in ethyl acetate/hexane affords 2.1 g (50%) of 3-[6-(4-heptylphenoxy)-1-oxohexyl]-4-hydroxy-2(5H)-furanone.

Quelle