Reaction #5343

Reaction equation

tetronic acid

triethylamine

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

palmitoleic acid

HCl

→

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

Yield 36.0%

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 1.07 g (10.72 mmol) of tetronic acid in 30 mL of dimethylformamide is added 1.64 mL (11.97 mmol) of triethylamine and 428 mg of 4-dimethylaminopyridine at 0° C. Next, 2.44 g (12.77 mmol) of 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride and 3.0 g (11.79 mmol) of palmitoleic acid are added and the reaction is stirred for 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 was obtained by flash chromatography with 10% methanol/ethyl acetate as eluant affording 1.3 g (36%) of 4-hydroxy-3-((Z)-1-oxo-9-hexadecenyl)-2(5H)-furanone.

Source