Reaction #5346

Reaction equation

tetronic acid

triethylamine

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

9-(4-chlorophenoxy)nonanoic acid

HCl

→

3-[9-(4-chlorophenoxy)-1-oxononyl]4-hydroxy-2(5H)-furanone

Yield 30.0%

Solvents

methanol ethyl acetate

dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted with four 50 mL portions of ether
2. 2
   DryingThe combined organic layers are dried over MgSO4
3. 3
   Concentrationconcentrated in vacuo
4. 4
   Otheraffording crude compound

Procedure

To a stirring solution of 736 mg (7.36 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.2 mL (8.09 mmol) of triethylamine and 300 mg of 4-dimethylaminopyridine at 0° C. Next, 1.7 g (8.86 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 2.6 g (8.06 mmol) of 9-(4-chlorophenoxy)nonanoic acid are added and the reaction is stirred overnight at room temperature. The reaction is acidified with 1.0 N HCl and extracted with four 50 mL portions of ether. The combined organic layers are dried over MgSO4 and concentrated in vacuo affording crude compound. Pure material is obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 800 mg (30%) of 3-[9-(4-chlorophenoxy)-1-oxononyl]4-hydroxy-2(5H)-furanone.

Source