Reaction #5342

Reaction equation

tetronic acid

triethylamine

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

myristoleic acid

HCl

→

4-hydroxy-3-((Z)-1-oxo-9-tetradecenyl)-2(5H)-furanone

Yield 82.0%

Solvents

methanol ethyl acetate

dimethylformamide

Conditions

Workup

1. 1
   Extractionextracted with four 100 mL portions of ethyl acetate
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 111 mg (1.11 mmol) of tetronic acid in 5 mL of dimethylformamide is added 185 μL (1.33 mmol) of triethylamine and 100 mg of 4-dimethylaminopyridine at 0° C. Next, 303 mg (1.33 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 300 mg (1.33 mmol) of myristoleic acid are added and the reaction mixture is stirred 3 days at room temperature. The reaction is acidified with 1.0N HCl and extracted with four 100 mL portions of ethyl acetate. 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 280 mg (82%) of 4-hydroxy-3-((Z)-1-oxo-9-tetradecenyl)-2(5H)-furanone.

Source