Reaction #5347

Reaction equation

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

Yield 50.0%

Solvents

dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted with three 200 mL portions of ether
2. 2
   DryingThe combined organic layers are dried over MgSO4
3. 3
   Concentrationconcentrated in vacuo

Procedure

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.

Source